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DOI: 10.1055/a-1829-0262
Catalyst-Controlled Chemodivergent [3+3] and [3+2] Formal Cycloadditions of Azomethine Ylides with Diphenylcyclopropenone
We thank the Ministerio de Ciencia e Innovación (MICINN) and Fondo Europeo de Desarrollo Regional (FEDER, UE) for financial support (Agencia Estatal de Investigación/Project PGC2018-098660-B-100). J. C. thanks the Ministerio de Educación Cultura y Deportes for a FPU fellowship. A. P. thanks the MICINN for a predoctoral fellowship.
Dedicated to Prof. Joan Bosch on the occasion of his retirement
Abstract
Chemodivergent cycloadditions of azomethine ylides with diphenylcyclopropenone involving either Cu-catalyzed [3+3] or Ag-catalyzed [3+2] processes have been developed. These transformations provide a highly efficient method for the preparation of a variety of aromatic substituted dihydropyridinones and dihydropyrrolones with excellent regio and diasteroselectivities.
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Key words
chemodivergent reactions - [3+3] and [3+2] cycloadditions - azomethine ylide - cyclopropenoneBiographical Sketches
Javier Corpas graduated with Honours in Chemistry from Universidad Autónoma de Madrid (UAM) in 2016 working on the development of novel catalytic asymmetric 1,3-dipolar cycloaddition reactions under the supervision of Dr. Javier Adrio and Prof. Dr. Juan C. Carretero. In 2017, he started his Ph.D. studies under the supervision of Dr. Ramón Gómez Arrayás and Dr. Pablo Mauleón in the group of Prof. Juan C. Carretero. In 2019 he carried out predoctoral work as a visiting student at Princeton University, USA, with Prof. Paul J. Chirik on the development of Fe-based catalysts for the selective H/D exchange of C–H bonds. His current research interests deal with the development of metal and photocatalytic methods for selective functionalization of unsaturated C–C bonds.
Alberto Ponce García completed his Ph.D. at the Department of Organic Chemistry (UAM) in 2017 under the supervision of Prof. Juan Carlos Carretero and Prof. Javier Adrio. From 2018 to 2020 he had a postdoctoral position at the Medicinal Chemistry Institute (CSIC) with Prof. Rosario González Muñiz, working on the synthesis of novel peptidomimetics. Since 2020 he works in the field of teaching organic chemistry for university students.
Ian Mac Lean Gariboldi completed his bachelor’s degree of Chemistry (2020) and master’s degree in Organic Chemistry (2021) at Universidad Autónoma de Madrid (Spain). During his master thesis, he worked with Prof. Dr. Diego J. Cardenas focusing his studies on Organometallic Chemistry. After finishing his studies, he joined Prof. Dr. Eva Blasco in an international traineeship at Ruprecht-Karls-Universität Heidelberg (Germany), mainly focused on the development of new polymer-based functional materials with application in 4D printing. He returned to the UAM where he is working on catalytic asymmetric cycloadditions under the supervision of Prof. Juan Carlos Carretero and Prof. Javier Adrio
Javier Adrio completed his Ph.D. thesis at the Department of Organic Chemistry (UAM), under the supervision of Prof. Juan Carlos Carretero. From 2001 to 2003 he worked on PharmaMar as a senior scientist; during this period he undertook postdoctoral studies at the University of Pennsylvania with Prof. Madeleine Joullié. He returned to the UAM as a Ramon y Cajal researcher until he was appointed Associate Professor in 2010. He has spent several short stays as a Visiting Scholar at the University of Pennsylvania working in Prof. Patrick Walsh’s lab. His research interest includes the development of catalytic asymmetric transition-metal-catalyzed methodologies.
Juan Carlos Carretero completed his Ph.D. at the Universidad Autónoma de Madrid (UAM) in 1985 under the direction of Prof. José L. García Ruano. From 1985 to 1988 he was a postdoctoral fellow at the Université Catholique de Louvain (Belgium) with Prof. León Ghosez. He subsequently joined the Department of Organic Chemistry of the UAM, where he became Associate Professor in 1988 and Professor in 2000. His current research interests are mainly focused on metal-catalyzed reactions, C–H functionalization processes and catalytic asymmetric cycloadditions.
The 1,3-dipolar cycloaddition between azomethine ylides and alkenes or alkynes has been intensely studied becoming one of the most used methodologies for the preparation of nitrogenated five-membered heterocycles via a [3+2] process.[1] Nevertheless, higher-order 1,3-dipolar cycloadditions for the synthesis of larger rings have been much less explored. Recently, the remarkable synthetic potential of this approach for the preparation of complex nitrogen heterocycles has encouraged several research groups to explore their feasibility. As a result, [6+3] cycloadditions between azomethine ylides and fulvenes,[2] tropones,[3] or acyl cycloheptatrienes[4] to afford piperidines have been developed. Stereoselective [3+3] cycloadditions using indolyl derivatives[5] or quinone monoimines[6] as dipolarophiles to deliver tetrahydrocarbolines or dihydrobenzoxazines have also been reported. Furthermore, the synthetic potential of [3+3] cycloadditions between azomethine ylides and other types of dipoles such as azomethine imines[7] or phthalazinium dicyanomethanides[8] is also known. In this context, the development of chemodivergent 1,3-dipolar cycloadditions of azomethine ylides, which could control the size of the heterocyclic adduct is a very appealing strategy for the efficient generation of molecular diversity.[9] However, examples of this modular chemoselective approach are very scarce.[10]
On the other hand, taking advantage of its high ring strain cyclopropenones have been extensively used as cycloaddition partners in the construction of structurally complex heterocycles via [3+2], [3+3], or two consecutive cyclizations.[11]
In these processes the cyclopropenone moiety can act as an electrophile by reaction either with the C=C or the C=O bond, as well as a nucleophile via activation with a Lewis base or a metal. More specifically, several cycloaddition reactions of cyclopropenone with different 1,3-dipoles have been developed.[12] Among them, to the best of our knowledge, only two examples of cycloadditions with azomethine ylides have been reported. Lown and co-workers[13] described a thermally-promoted reaction between azomethine ylides generated from 3-aroylaziridines and diphenylcyclopropenone. The authors suggested that the reaction occurs via an unexpected formation of a carbonyl ylide and subsequent [3+2] cycloaddition with the generated imine (Scheme [1]A).
More recently, an organocatalytic asymmetric cycloaddition between azomethine ylides derived from o-hydroxybenzaldehyde and cyclopropenones has been reported. In this case, Xu and co-workers[14] proposed an initial [3+2] cycloaddition across the double bond of the cyclopropenone. Subsequent ring-opening cyclization would lead to two different regioisomers based on the substitution at the cyclopropenone. The reaction at the carbonyl generates the lactone whereas the annulation at the α-position gives rise to the benzofuran (Scheme [1]B).
As part of our group’s ongoing work to explore strain-promoted 1,3-dipolar cycloadditions of azomethine ylides,[15] herein we describe a divergent synthesis of nitrogenated heterocycles by metal-catalyzed 1,3-dipolar cycloaddition between azomethine ylides and cyclopropenones.
a Isolated yield (0.1 mmol scale).
b By 1H NMR analysis on the crude mixtures.
c 2a: 2.5 equiv.
d ee by HPLC: 15%.
e Racemic product.
We began our studies employing cyclopropenone 1 and iminoester 2a as model substrates to optimize the reaction conditions. After screening a variety of metal salts and bases using (±)-BINAP as a ligand in THF, we observed the formation of a 1:1 diastereoisomeric mixture of lactams 3a using Cu(CH3CN)4PF6 and KO t Bu as a base (Table [1], entry 4). The yield of the mixture of [3+3] diastereoisomeric cycloadducts was improved up to 37% with Segphos as a ligand (entry 5). An additional increase in the yield was observed in toluene (50%, entry 6). To our delight, a crucial improvement of the diastereoselectivity was achieved using DBU as the base, the trans-isomer being exclusively detected albeit in a lower yield (24%, entry 7). Moreover, the yield of trans-3a was improved further to 48% by increasing the amount of iminoester 2a up to 2.5 equivalents and to 68% using a 3:1 mixture of toluene:THF as solvent (entries 8 and 9). Unfortunately, the enantioselectivity was rather poor (15% ee).
It is interesting to note that no [3+3] cycloaddition was observed in the absence of ligand, the formation of the [3+2] adducts 4 and 5 in low yield being detected exclusively (Table [1], entry 10). Inspired by this observation, we carried out a screening of reaction conditions aimed at controlling the selectivity of the [3+2] cycloaddition. Among the ligands tested the monodentate (R)-Monophos afforded a 1:1 mixture of pyrrolones 4a and 5a in 16% yield (entry 11). A significative increase in the reactivity and regioselectivity was observed when silver salts were used in the reaction. Thus, the adduct 4a was isolated in a 52% yield when AgOAc was used as metal source in toluene (entry 12). A further increase in the reaction yield up to 73%, while maintaining the regioselectivity levels, was observed changing the silver salt to AgNO3 (entry 13).
In summary, we found appropriate reaction conditions to either the [3+3] cycloaddition [Cu(CH3CN)4PF6/(R)-Segphos, DBU, entry 9] or the [3+2] process [AgNO3/(R)-Monophos, DBU, Table [1], entry 13].
With these two sets of optimal reaction conditions in hand, we first studied the scope of the process regarding the substitution at the azomethine ylide. As shown in Scheme [2], the copper-catalyzed [3+3] process worked well for all the aromatic iminoesters tested. Thus, substrates 2b–e with electron-donating substituents at any position at the aromatic ring provided the trans-dihydropyridinones 3b–e with almost complete diastereoselectivity and in moderate to good yields. Similar results were obtained from a variety of electron-poor iminoesters (adducts 3f,g). Naphthyl derivative 2h also underwent the cycloaddition providing the corresponding adduct 3h in 71% yield. Interestingly, the reaction with the more challenging alanine-derived iminoester took place in a reasonable 57% yield affording the dihydropyridinone 3i with a quaternary center at C-5, albeit with lower diastereoselectivity. The relative configuration of adducts trans-3 was unequivocally established by X-ray diffraction analysis of the dihydropyridinone trans-3a (see SI for details).[16]
We next explored the scope of the formation of dihydropyrrolones through the [3+2] process (Scheme [3]). A variety of iminoesters derived from aromatic aldehydes reacted with cyclopropenone 1 to afford the corresponding adducts regardless of the electron-donating (substrates 4b,d,e) or electron-withdrawing (substrates 4g,j,k) character of the substituent at the aromatic ring of the azomethine ylide precursor.
The naphthyl and thienyl iminoesters 2h and 2l, also proved to be excellent substrates in this transformation. The structure of dihydropyrrolones 4 was confirmed by X-ray diffraction analysis of 4g.[17]
A tentative mechanism to explain the chemodivergent [3+3] or [3+2] cycloaddition between azomethine ylides and cyclopropenone 2 is shown in Scheme [4]. First, the metalated azomethine ylide I was formed by coordination of the iminoester with the copper salt and deprotonation. The subsequent 1,4-addition of the ylide to the cyclopropenone would lead to the formation of intermediate II. The ring-opening process of the highly strained cyclopropene with the concomitant displacement of the iminium moiety, assisted by the coordination of the nitrogen with the metal complex, would give the ketene III. Then, intramolecular nucleophilic addition of the carbonyl to the ketene would generate an oxonium cation which would evolve to the lactone IV.[18] Finally, the 1,2-addition of the imine complex formed in the previous step to the lactone unit, followed by opening and cyclization would provide the final lactam 3 with trans relative configuration.
A different reaction pathway occurs in the reaction catalyzed by Ag/(R)-Monophos. In this case, we propose a 1,2-addition of the nitrogen of the iminoester to the carbonyl group of the cyclopropenone with the assistance of the silver salt[19] leading to the intermediate VI, which could isomerize to VII in the presence of DBU. Subsequent ring-opening of the three-membered ring and cyclization by nucleophilic addition to the C=N bond would give the pyrrolone 4 (Scheme [4]).
Additionally, the hydrogenation of the C=C bond in the dihydropyridinones cis-3a and trans-3a was performed using standard conditions [H2/Pd(C) 10 mol%, in MeOH]. The reaction with cis-3a afforded selectively the lactam 5 (77% yield), while the hydrogenation of trans-3a led to a mixture of diastereomeric lactams 6 and 7 (98% yield, Scheme [5]).
In conclusion, a chemodivergent [3+3] and [3+2] formal cycloaddition of azomethine ylides and diphenylcyclopropenone has been developed by switching the catalyst. These reactions provide modular, highly selective, one-pot approaches to a variety of dihydropyridinones and dihydropyrrolones through a Cu/(R)-Segphos [3+3] cycloaddition or Ag/(R)-Monophos [3+2] cycloaddition catalyzed processes. The readily available starting materials, and good regio- and diastereoselectivity make this protocol an attractive alternative for the preparation of aryl-substituted five- and six-membered lactam derivatives.
All air- and moisture-sensitive manipulations were carried out in anhydrous solvents and under argon. Toluene and THF were dried over the PureSolv MD purification system. Melting points were taken in open-end capillary tubes. Reactions were monitored by TLC carried out on 0.25 mm silica gel plates (230–400 mesh). Flash column chromatography was performed using silica gel (230–400 mesh). NMR spectra were recorded on 300 or 75 MHz instrument and calibrated using residual non-deuterated solvent (CDCl3) as internal reference (δH = 7.26, δC =77.2 for CDCl3). HRMS spectra were recorded on a TOF mass spectrometer with electrospray ionization (ESI) as the ionization source. The chromatograms of the racemic and enantiomerically enriched cycloadducts were obtained by HPLC or SFC. α-Iminoesters were prepared by condensation of methyl glycinate hydrochloride and the corresponding aldehydes.[20] Due to their lability, all α-iminoesters once isolated were immediately used in the 1,3-dipolar cycloaddition without further purification.
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Cu-Catalyzed [3+3] Cycloaddition of 2,3-Diphenylcyclopropenone (1) with Iminoesters 2; General Procedure 1
In a 25 mL flask charged with a magnetic stirrer were added Cu(CH3CN)4PF6 (18.6 mg, 0.05 mmol) and (R)-Segphos (30.5 mg, 0.05 mmol). The flask was closed with a septum and the air was replaced by an argon atmosphere. Toluene (2 mL) was added, and the white suspension was stirred for 15 min. After that, a solution of the iminoester 2 (1.25 mmol, 2.5 equiv) in toluene:THF (0.9:0.6 mL) was added under argon atmosphere, and the resulting solution was stirred for 10 min. Finally, DBU (11.2 μL, 0.075 mmol) was added to the reaction flask followed by the dropwise addition of a solution of the 2,3-diphenylcyclopropenone (1; 103.1 mg, 0.5 mmol) in toluene:THF (0.9:0.6 mL). The reaction mixture was stirred for 16 h at rt, diluted with EtOAc (20 mL) and with a solution of sat aq NH4Cl (25 mL). The aqueous phase was extracted with EtOAc (2 × 20 mL) and the combined organic phases were washed with H2O (50 mL) and brine (50 mL), dried (Na2SO4), and filtered. The solvent was removed in vacuo and the resulting residue was purified by column chromatography (toluene:EtOAc 10:1). The corresponding dihydropyridinone was further purified by recrystallization from a mixture of CH2Cl2 and n-pentane in the fridge to afford white crystals, which were collected by filtration and dried in the rotatory evaporator.
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(±)-Methyl trans-3,4,6-Triphenyl-5,6-dihydropyridin-2-one-5-carboxylate (trans-3a)
Following the general procedure 1, the reaction of methyl 2-(benzylideneamino)acetate iminoester (2a; 221 mg, 1.25 mmol) afforded the title compound as a white solid after recrystallization (130 mg, 68%); mp 198–201 °C.
1H NMR (300 MHz, CDCl3): δ = 7.51–7.33 (m, 5 H), 7.18–7.10 (m, 3 H), 7.11–6.99 (m, 5 H), 6.82–6.66 (m, 2 H), 6.31 (s, 1 H), 5.32 (d, J = 4.1 Hz, 1 H), 3.98 (d, J = 4.3 Hz, 1 H), 3.64 (s, 3 H).
13C NMR (75 MHz, CDCl3): δ = 170.6, 165.7, 143.1, 139.7, 138.7, 134.5, 134.0, 130.8 (2 C), 129.0 (2 C), 128.3, 128.2 (2 C), 127.9 (2 C), 127.7, 127.5 (2 C), 127.3, 126.2 (2 C), 56.7, 54.5, 52.7.
HRMS (ESI+): m/z [M + H]+ calcd for C25H22NO3: 384.1521; found: 384.1580.
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(±)-Methyl cis-3,4,6-Triphenyl-5,6-dihydropyridin-2-one-5-carboxylate (cis-3a)
Following the general procedure 1, the reaction of methyl 2-(benzylideneamino)acetate iminoester (2a; 148 mg, 0.84 mmol) and cyclopropenone 1 (57 mg, 0.28 mmol) using KO t Bu (1 M in THF, 0.056 mmol) as base, afforded after column chromatography a 1:1 mixture of (±)-cis-3a (27 mg, 25%) and trans-3a (27 mg, 25%); mp 199–202 °C.
1H NMR (300 MHz, CDCl3): δ = 7.45–7.33 (m, 5 H, Ar), 7.21–7.19 (m, 5 H, Ar), 7.17–7.11 (m, 3 H, Ar), 7.06–6.93 (m, 2 H, Ar), 5.83 (s, 1 H, NH), 5.37 (d, J = 5.1 Hz, 1 H, H1), 3.84 (d, J = 5.0 Hz, 1 H, H2), 3.41 (s, 3 H, CH3O).
13C NMR (75 MHz, CDCl3): δ = 168.7, 166.8, 144.6, 138.4, 137.6, 134.9, 134.5, 131.1 (2 C), 129.0 (2 C), 128.9, 128.6 (2 C), 128.2 (2 C), 128.1, 127.6 (2 C), 127.3, 126.3 (2 C), 57.4, 54.7, 52.1.
HRMS (ESI+): m/z [M + H]+ calcd for C25H22NO3: 384.1600; found: 384.1588.
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(±)-Methyl trans-6-(4-Methoxyphenyl)-3,4-diphenyl-5,6-dihydropyridin-2-one-5-carboxylate (trans-3b)
Following the general procedure 1 the reaction of methyl 2-((4-methoxybenzylidene)amino)acetate iminoester (2b) (259 mg, 1.25 mmol) afforded the title compound as a white solid after recrystallization (107 mg, 52%); mp 190–193 °C.
1H NMR (300 MHz, CDCl3): δ = 7.36 (d, J = 8.5 Hz, 2 H), 7.20–7.02 (m, 8 H), 6.94 (d, J = 8.5 Hz, 2 H), 6.79 (dd, J = 6.6, 3.0 Hz, 2 H), 6.16 (br s, 1 H), 5.26 (d, J = 3.9 Hz, 1 H), 3.97 (d, J = 4.9 Hz, 1 H), 3.83 (s, 3 H), 3.59 (s, 3 H).
13C NMR (75 MHz, CDCl3): δ = 170.8, 165.9, 159.8, 143.6, 138.7, 134.8, 131.7, 130.9, 128.4, 128.0, 127.8, 127.7, 127.6, 127.4, 114.4, 56.4, 55.5, 55.3, 52.8.
HRMS (TOF MS EI+): m/z [M]+ calcd for C26H23NO4: 413.1627; found: 413.1617.
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(±)-Methyl trans-6-(4-(Methylthio)phenyl)-3,4-diphenyl-5,6-dihydropyridin-2-one-5-carboxylate (trans-3c)
Following the general procedure 1, the reaction of methyl 2-((4-(methylthio)benzylidene)amino)acetate iminoester (2c; 279 mg, 1.25 mmol) afforded the title compound as a white solid after recrystallization (94 mg, 44%); mp 194–197 °C.
1H NMR (300 MHz, CDCl3): δ = 7.43 (d, J = 8.3 Hz, 2 H), 7.35 (d, J = 8.9 Hz, 2 H), 7.27–7.19 (m, 3 H), 7.19–7.10 (m, 5 H), 6.90–6.79 (m, 2 H), 6.21 (d, J = 3.5 Hz, 1 H), 5.35 (t, J = 4.0 Hz, 1 H), 4.03 (d, J = 4.4 Hz, 1 H), 3.70 (s, 3 H), 2.59 (s, 3 H).
13C NMR (75 MHz, CDCl3): δ = 170.7, 164.4, 139.0, 138.7, 136.5, 134.6, 130.9, 130.1, 128.4, 128.0, 127.9, 127.7, 127.4, 126.9, 126.8, 125.3, 56.2, 55.0, 52.9, 15.7.
HRMS (TOF MS EI+): m/z [M]+ calcd for C26H23NO3S: 429.1399; found: 429.1402.
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(±)-Methyl trans-3,4-Diphenyl-6-(m-tolyl)-5,6-dihydropyridin-2-one-5-carboxylate (trans-3d)
Following the general procedure 1, the reaction of methyl 2-((3-methylbenzylidene)amino)acetate iminoester (2d; 239 mg, 1.25 mmol) afforded the title compound as a white solid after recrystallization (123 mg, 62%); mp 195–197 °C.
1H NMR (300 MHz, CDCl3): δ = 7.33–7.30 (m, 1 H), 7.21–7.10 (m, 5 H), 7.08–7.03 (m, 6 H), 6.78 (dd, J = 6.6, 3.0 Hz, 2 H), 6.63 (br s, 1 H), 5.28 (t, J = 4.0 Hz, 1 H), 3.98 (d, J = 4.0 Hz, 1 H), 3.64 (s, 3 H), 2.38 (s, 3 H).
13C NMR (75 MHz, CDCl3): δ = 170.78, 165.96, 143.05, 139.83, 138.80, 138.65, 134.74, 134.04, 130.83, 128.98, 128.81, 128.31, 127.89, 127.67, 127.56, 127.23, 127.00, 123.39, 56.44, 54.92, 52.73, 21.56.
HRMS (ESI+): m/z [M + H ]+ calcd for C26H24NO3: 398.1751; found: 398.1752.
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(±)-Methyl trans-6-(6-Bromobenzo[d][1,3]dioxol-5-yl)-3,4-diphenyl-5,6-dihydropyridin-2-one-5-carboxylate (trans-3e)
Following the general procedure 1, the reaction of methyl 2-(((6-bromobenzo[d][1,3]dioxol-5-yl)methylene)amino)acetate iminoester (2e; 375 mg, 1.25 mmol) afforded the title compound as a white solid after recrystallization (149 mg, 59%); mp 189–190 °C.
1H NMR (300 MHz, CDCl3): δ = 7.18 (br s, 5 H), 7.16–7.13 (m, 3 H), 7.07 (s, 1 H), 7.05–6.98 (m, 3 H), 6.10 (d, J = 9.6 Hz, 1 H), 6.02 (s, 2 H), 5.65 (d, J = 5.3 Hz, 1 H), 4.10 (d, J = 5.2 Hz, 1 H), 3.47 (s, 3 H).
13C NMR (75 MHz, CDCl3): δ = 168.7, 167.3, 148.6, 148.2, 145.0, 138.4, 134.8, 131.2, 129.6, 128.8, 128.3, 128.2, 127.7, 127.4, 113.9, 113.4, 107.3, 107.2, 102.3, 56.5, 52.4, 51.3.
HRMS (ESI+): m/z [M + H]+ calcd for C26H21BrNO5: 506.0598; found: 506.0592.
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(±)-Methyl trans-6-(4-(Methoxycarbonyl)phenyl)-3,4-diphenyl-5,6-dihydropyridin-2-one-5-carboxylate (trans-3f)
Following the general procedure 1, the reaction of methyl 4-(((2-methoxy-2-oxoethyl)imino)methyl)benzoate iminoester (2f; 294 mg, 1.25 mmol) afforded the title compound as a white solid after recrystallization (79.5 mg, 36%); mp 185–187 °C.
1H NMR (300 MHz, CDCl3): δ = 8.10 (d, J = 8.0 Hz, 2 H), 7.49 (d, J = 8.0 Hz, 2 H), 7.25–7.09 (m, 8 H), 7.11–6.86 (m, 2 H), 6.00 (br s, 1 H), 5.43 (d, J = 5.1 Hz, 1 H), 3.94 (s, 3 H), 3.86 (d, J = 5.1 Hz, 1 H), 3.40 (s, 3 H).
13C NMR (75 MHz, CDCl3): δ = 170.5, 168.6, 166.6, 149.3, 142.6, 138.4, 134.9, 131.2, 130.9, 130.9, 130.4, 128.7, 128.4, 127.8, 127.6, 126.6, 126.4, 57.4, 54.4, 52.4, 52.4.
HRMS (TOF MS EI+): m/z [M]+ calcd for C27H23NO5: 441.1576; found: 441.1582.
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(±)-Methyl trans-6-(3-Cyanophenyl)-3,4-diphenyl-5,6-dihydropyridin-2-one-5-carboxylate (trans-3g)
Following the general procedure 1, the reaction of methyl 2-((3-cyanobenzylidene)amino)acetate iminoester (2g; 253 mg, 1.25 mmol) afforded the title compound as a white solid after recrystallization (114.3 mg, 56%); mp 182–184 °C.
1H NMR (300 MHz, CDCl3): δ = 7.69–7.61 (m, 1 H), 7.65–7.54 (m, 2 H), 7.51–7.42 (m, 1 H), 7.12–7.03 (m, 4 H), 7.03–6.92 (m, 5 H), 6.70–6.60 (m, 2 H), 5.25 (t, J = 3.9 Hz, 1 H), 3.83 (d, J = 3.5 Hz, 1 H), 3.61 (s, 3 H).
13C NMR (75 MHz, CDCl3): δ = 170.2, 166.0, 142.7, 141.8, 138.4, 134.3, 132.0, 130.8, 130.0, 129.9, 129.6, 128.2, 128.1, 128.0, 127.7, 127.5, 118.4, 113.2, 55.6, 54.3, 53.1.
HRMS (ESI+): m/z [M + H]+ calcd for C26H21N2O3: 409.1547; found: 409.1550.
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(±)-Methyl trans-6-(Naphthalen-2-yl)-3,4-diphenyl-5,6-dihydropyridin-2-one-5-carboxylate (trans-3h)
Following the general procedure 1, the reaction of methyl 2-((naphthalen-2-ylmethylene)amino)acetate iminoester (2h; 284 mg, 1.25 mmol) afforded the title compound as a white solid after recrystallization (153 mg, 71%); mp 200–204 °C.
1H NMR (300 MHz, CDCl3): δ = 7.95–7.80 (m, 4 H), 7.63–7.44 (m, 3 H), 7.15 (br s, 3 H), 7.12–6.94 (m, 5 H), 6.80–6.65 (m, 2 H), 6.44 (s, 1 H), 5.60–5.38 (d, J = 3.8 Hz, 1 H), 4.10 (d, J = 3.6 Hz, 1 H), 3.66 (s, 3 H).
13C NMR (75 MHz, CDCl3): δ = 170.8, 157.1, 143.5, 143.4, 138.8, 137.1, 134.6, 133.4, 133.2, 130.9, 129.2, 128.4, 128.3, 128.0, 127.9, 127.8, 127.7, 127.4, 126.8, 126.7, 125.6, 124.0, 56.7, 54.8, 53.0.
HRMS (ESI+): m/z [M + H]+ calcd for C29H24NO3: 434.1751; found: 434.1750.
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(±)-Ethyl 3-Methyl-3,4,6-triphenyl-5,6-dihydropyridin-2-one-5-carboxylate (trans/cis-3i)
Following the general procedure 1, the reaction of ethyl 2-(benzylideneamino)propanoate iminoester (2i; 257 mg, 1.25 mmol) afforded a trans/cis mixture of the title compound as a colorless oil after column chromatography (154 mg, 57%, trans:cis = 22:78).
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trans-3i
1H NMR (300 MHz, CDCl3): δ = 7.40 (br s, 5 H), 7.18–7.01 (m, 10 H), 6.04 (s, 1 H), 5.59 (s, 1 H), 4.03–3.80 (m, 2 H), 1.41 (s, 3 H), 1.02 (t, J = 7.1 Hz, 3 H).
13C NMR (75 MHz, CDCl3): δ = 172.5, 166.3, 151.9, 137.3, 136.4, 135.2, 130.8, 129.0, 128.8, 128.7, 128.1, 127.7, 127.6, 127.5, 127.1, 61.6, 61.4, 54.8, 17.4, 13.8.
HRMS (ESI+): m/z [M + H]+ calcd for C27H26NO3: 412.1907; found: 412.1911.
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cis-3i
1H NMR (300 MHz, CDCl3): δ = 7.38 (hept, J = 3.8 Hz, 5 H), 7.12 (dq, J = 5.2, 3.3, 2.6 Hz, 6 H), 7.03 (dd, J = 7.5, 2.0 Hz, 2 H), 6.88–6.82 (m, 2 H), 5.91 (s, 1 H), 4.95 (s, 1 H), 4.19 (qd, J = 7.1, 4.5 Hz, 2 H), 1.25 (t, J = 7.1 Hz, 3 H), 1.10 (s, 3 H).
13C NMR (75 MHz, CDCl3): δ = 170.7, 166.5, 151.0, 137.7, 137.1, 135.8, 130.6, 129.3, 128.8, 128.4, 128.2, 128.1, 127.5, 127.4, 127.0, 64.9, 61.8, 52.7, 21.3, 14.1.
HRMS (ESI+): m/z [M + H]+ calcd for C27H26NO3: 412.1907; found: 412.1913.
#
Ag-Catalyzed [3+2] Cycloaddition of 2,3-Diphenylcyclopropenone (1) with Iminoesters 2; General Procedure 2
In a 25 mL flask charged with a magnetic stirrer were added AgNO3 (8 mg, 0.05 mmol) and (R)-MonoPhos (36 mg, 0.1 mmol). The flask was closed with a septum and the air was replaced by an argon atmosphere. Toluene (2 mL) was added, and the resulting solution was stirred 15 min in the dark. After that, a solution of the iminoester 2 (0.75 mmol, 1.5 equiv) in toluene:THF (0.88:0.62 mL) was added under argon atmosphere, and the resulting solution was stirred for 10 min. Finally, DBU (11 μL, 0.075 mmol) was added to the reaction flask followed by the dropwise addition of a solution of the 2,3-diphenylcyclopropenone (1; 103.1 mg, 0.5 mmol) in toluene:THF (0.88:0.62 mL). The reaction mixture was stirred 24 h at rt and diluted with EtOAc (20 mL) and sat aq NH4Cl (25 mL). The aqueous phase was extracted with EtOAc (2 × 20 mL) and the combined organic phases were washed with H2O (50 mL) and brine (50 mL), dried (Na2SO4), and filtered. The solvent was removed in vacuo and the resulting residue was further purified by column chromatography (toluene:EtOAc 10:1).
#
(±)-Methyl 1-(Benzyl)-3,4-diphenyl-1,5-dihydro-2-pyrrol-2-one-5-carboxylate (4a)
Following the general procedure 2, the reaction of methyl 2-(benzylideneamino)acetate iminoester (2a; 132 mg, 0.75 mmol) afforded the title compound as a yellowish oil after column chromatography (140 mg, 73%).
1H NMR (300 MHz, CDCl3): δ = 7.48–7.25 (m, 15 H), 5.23 (d, J = 14.9 Hz, 1 H), 5.04 (s, 1 H), 4.31 (d, J = 14.9 Hz, 1 H), 3.50 (s, 3 H).
13C NMR (75 MHz, CDCl3): δ = 170.4, 168.1, 147.0, 136.3, 133.1, 131.3, 130.9, 129.5, 129.3, 128.7, 128.7, 128.5, 128.4, 128.2, 127.8, 64.9, 52.6, 45.6.
HRMS (ESI+): m/z [M + H]+ calcd for C25H22NO3: 384.1594; found: 384.1596.
#
(±)-Methyl 1-(4-Methoxybenzyl)-3,4-diphenyl-1,5-dihydro-2-pyrrol-2-one-5-carboxylate (4b)
Following the general procedure 2, the reaction of methyl 2-((4-methoxybenzylidene)amino)acetate iminoester (2b; 155 mg, 0.75 mmol) afforded the title compound as a yellowish oil after column chromatography (122 mg, 59%).
1H NMR (300 MHz, CDCl3): δ = 7.42 (dd, J = 6.7, 3.1 Hz, 2 H), 7.33–7.20 (m, 10 H), 6.89 (d, J = 8.7 Hz, 2 H), 5.14 (d, J = 14.7 Hz, 1 H), 4.98 (s, 1 H), 4.20 (d, J = 14.8 Hz, 1 H), 3.81 (s, 3 H), 3.48 (s, 3 H).
13C NMR (75 MHz, CDCl3): δ = 170.4, 168.3, 159.4, 147.0, 133.4, 131.6, 131.0, 130.2, 129.7, 129.4, 128.6, 128.5, 128.5, 128.5, 128.3, 114.2, 64.8, 55.4, 52.7, 45.1.
HRMS (ESI+): m/z [M + H]+ calcd for C26H24NO4: 414.1700; found: 414.1698.
#
(±)-Methyl 1-(3-Methylbenzyl)-3,4-diphenyl-1,5-dihydro-2-pyrrol-2-one-5-carboxylate (4d)
Following the general procedure 2, the reaction of methyl 2-((3-methylbenzylidene)amino)acetate iminoester (2d; 143 mg, 0.75 mmol) afforded the title compound as a white solid after column chromatography (131.2 mg, 66%); mp 186–188 °C.
1H NMR (300 MHz, CDCl3): δ = 7.48–7.41 (m, 2 H), 7.35–7.22 (m, 9 H), 7.17–7.10 (m, 3 H), 5.20 (d, J = 14.8 Hz, 1 H), 5.03 (s, 1 H), 4.21 (d, J = 14.8 Hz, 1 H), 3.49 (s, 3 H), 2.37 (s, 3 H).
13C NMR (75 MHz, CDCl3): δ = 170.5, 168.3, 147.0, 138.7, 136.4, 133.4, 131.6, 131.1, 129.7, 129.6, 129.4, 128.8, 128.7, 128.6, 128.6, 128.5, 128.4, 125.9, 64.9, 52.7, 45.7, 21.5.
HRMS (ESI+): m/z [M + H]+ calcd for C26H24NO3: 398.1751; found: 398.1748.
#
(±)-Methyl 1-((6-Bromobenzo[d][1,3]dioxol-5-yl)methyl)-3,4-diphenyl-1,5-dihydro-2-pyrrol-2-one-5-carboxylate (4e)
Following the general procedure 2, the reaction of methyl 2-(((6-bromobenzo[d][1,3]dioxol-5-yl)methylene)amino)acetate iminoester (2e; 225 mg, 0.75 mmol) afforded the title compound as a white solid after column chromatography (184.8 mg, 73%); mp 179–181 °C.
1H NMR (300 MHz, CDCl3): δ = 7.45–7.39 (m, 2 H), 7.31–7.23 (m, 8 H), 7.01 (s, 1 H), 6.93 (s, 1 H), 5.97 (s, 2 H), 5.16 (d, J = 15.2 Hz, 1 H), 5.11 (s, 1 H), 4.45 (d, J = 15.1 Hz, 1 H), 3.53 (s, 3 H).
13C NMR (75 MHz, CDCl3): δ = 170.6, 168.2, 148.3, 148.0, 147.3, 133.2, 131.4, 130.9, 129.7, 129.5, 129.0, 128.8, 128.6, 128.5, 128.4, 114.5, 112.7, 110.8, 102.0, 65.1, 52.8, 45.4.
HRMS (ESI+): m/z [M + H]+ calcd for C26H21BrNO5: 506.0598; found: 506.0596.
#
(±)-Methyl 1-(3-Cyanobenzyl)-3,4-diphenyl-1,5-dihydro-2-pyrrol-2-one-5-carboxylate (4g)
Following the general procedure 2, the reaction of methyl 2-((3-cyanobenzylidene)amino)acetate iminoester (2g; 151 mg, 0.75 mmol) afforded the title compound as a white solid after column chromatography (143 mg, 70%); mp 181–184 °C.
1H NMR (300 MHz, CDCl3): δ = 7.64–7.58 (m, 3 H), 7.51–7.41 (m, 3 H), 7.35–7.28 (m, 5 H), 7.26–7.20 (m, 3 H), 5.11 (d, J = 15.3 Hz, 1 H), 5.02 (s, 1 H), 4.40 (d, J = 15.3 Hz, 1 H), 3.46 (s, 3 H).
13C NMR (75 MHz, CDCl3): δ = 170.7, 168.0, 147.4, 138.2, 133.1, 132.0, 131.7, 131.3, 130.7, 129.8, 129.7, 129.6, 128.7, 128.7, 128.5, 128.4, 118.5, 113.0, 65.1, 52.8, 45.1.
HRMS (ESI+): m/z [M + H]+ calcd for C26H21N2O3: 409.1547; found: 409.1545.
#
(±)-Methyl 1-(Naphthalen-2-ylmethyl)-3,4-diphenyl-1,5-dihydro-2-pyrrol-2-one-5-carboxylate (4h)
Following the general procedure 2, the reaction of methyl 2-((naphthalen-2-ylmethylene)amino)acetate iminoester (2h; 170.4 mg, 0.75 mmol) afforded the title compound as an oil after column chromatography (176 mg, 81%).
1H NMR (300 MHz, CDCl3): δ = 7.92–7.84 (m, 3 H), 7.80 (s, 1 H), 7.56–7.45 (m, 5 H), 7.35 (dd, J = 4.8, 2.1 Hz, 3 H), 7.31–7.20 (m, 5 H), 5.41 (d, J = 14.9 Hz, 1 H), 5.05 (s, 1 H), 4.45 (d, J = 14.9 Hz, 1 H), 3.45 (s, 3 H).
13C NMR (75 MHz, CDCl3): δ = 170.6, 168.3, 152.9, 147.2, 134.0, 133.5, 133.1, 131.5, 131.0, 129.7, 129.5, 128.9, 128.6, 128.6, 128.4, 126.8, 126.5, 126.3, 124.4, 124.0, 117.9, 111.2 65.0, 52.7, 45.9.
HRMS (ESI+): m/z [M + H]+ calcd for C29H24NO3: 434.1751; found: 434.1762.
#
(±)-Methyl 1-(4-Bromobenzyl)-3,4-diphenyl-1,5-dihydro-2-pyrrol-2-one-5-carboxylate (4j)
Following the general procedure 2 the reaction of methyl 2-((4-bromobenzylidene)amino)acetate iminoester (2j; 191 mg, 0.75 mmol) afforded the title compound as an oil after column chromatography (115.6 mg, 50%).
1H NMR (300 MHz, CDCl3): δ = 7.49–7.41 (m, 4 H), 7.32–7.19 (m, 10 H), 4.93 (d, J = 15.3 Hz, 1 H), 4.69 (br s, 1 H), 4.24 (d, J = 15.4 Hz, 1 H), 3.27 (s, 3 H).
13C NMR (75 MHz, CDCl3): δ = 171.3, 169.8, 149.0, 135.7, 133.7, 131.5, 131.2, 130.9, 130.2, 129.8, 129.4, 128.8, 128.8, 128.7, 128.3, 121.8, 88.3, 53.9, 41.9.
HRMS (ESI+): m/z [M + OH]+ calcd for C25H21BrNO4: 478.0648; found: 478.0642.
#
(±)-Methyl 3,4-Diphenyl-1-(4-(trifluoromethyl)benzyl)-1,5-dihydro-2-pyrrol-2-one-5-carboxylate (4k)
Following the general procedure 2 the reaction of methyl 2-((4-(trifluoromethyl)benzylidene)amino)acetate iminoester (2k; 184 mg, 0.75 mmol) afforded the title compound as an oil after column chromatography (176.1 mg, 78%).
1H NMR (300 MHz, CDCl3): δ = 7.63 (d, J = 7.9 Hz, 2 H), 7.48–7.42 (m, 4 H), 7.33–7.30 (m, 3 H), 7.25–7.20 (m, 3 H), 5.18 (d, J = 14.9 Hz, 1 H), 5.01 (s, 1 H), 4.39 (d, J = 14.9 Hz, 1 H), 3.45 (s, 3 H).
13C NMR (75 MHz, CDCl3): δ = 170.7, 168.1, 147.3, 140.6, 133.3, 131.5, 130.9, 130.6, 129.7, 129.7, 129.1, 128.9, 128.7, 128.6, 128.5, 125.9 (q, J = 3.8 Hz), 123.8 (q, J = 153 Hz), 65.1, 52.8, 45.4.
HRMS (ESI+): m/z [M + H]+ calcd for C26H21F3NO3: 452.1468; found: 452.1479.
#
(±)-Methyl 3,4-Diphenyl-1-(thiophen-2-ylmethyl)-1,5-dihydro-2-pyrrol-2-one-5-carboxylate (4l)
Following the general procedure 2, the reaction of methyl 2-((thiophen-2-ylmethylene)amino)acetate iminoester (2l; 137.4 mg, 0.75 mmol) afforded the title compound as a yellow oil after column chromatography (125 mg, 64%).
1H NMR (300 MHz, CDCl3): δ = 7.47 (dd, J = 6.6, 3.1 Hz, 2 H), 7.33–7.16 (m, 14 H), 4.98 (d, J = 15.2 Hz, 1 H), 4.64 (s, 1 H), 4.22 (d, J = 15.2 Hz, 1 H), 3.23 (s, 3 H), 2.46 (s, 3 H).
13C NMR (75 MHz, CDCl3): δ = 171.5, 169.7, 148.9, 138.0, 133.8, 133.4, 131.3, 130.4, 129.8, 129.8, 129.4, 128.9, 128.8, 128.3, 126.5, 88.3, 53.9, 42.1, 16.0.
#
Hydrogenation of Dihydropyridinones cis-3a and trans-3a; General Procedure 3
To a solution of the corresponding dihydropyridinone (0.03 mmol) in MeOH (4 mL) was added 10% Pd/C (35 mg) at rt. The flask was closed with a septum and evacuated and flushed with H2. The reaction mixture was stirred under H2 atmosphere (1 atm) for 12 h, diluted with CH2Cl2, and filtered through Celite, The solvent was removed in vacuo and the resulting residue was purified by column chromatography (cyclohexane:EtOAc 1:1).
#
(±)-Methyl (3S*,4S*,5S*,6R*)-3,4,6-Triphenylpyridin-2-one-5-carboxylate (5)
Following the general procedure 3, the reaction of cis-3a (13 mg, 0.03 mmol) afforded the title compound as a white solid after column chromatography (10 mg, 77%); mp 188–191 °C.
1H NMR (300 MHz, CDCl3): δ = 7.47–7.30 (m, 3 H), 7.20–7.05 (m, 10 H), 6.80–6.86 (m, 2 H), 6.27 (s, 1 H), 5.15 (d, J = 4.9 Hz, 1 H), 4.38 (d, J = 8.8 Hz, 1 H), 4.08 (dd, J = 8.8, 6.8 Hz, 1 H), 3.53 (dd, J = 6.6, 5.0 Hz, 1 H), 3.02 (s, 3 H).
13C NMR (75 MHz, CDCl3): δ = 173.4, 170.2, 138.1, 137.6, 136.1, 131.6 (2 C), 129.8 (2 C), 128.8 (2 C), 128.5, 127.8 (2 C), 127.2, 127.1 (2 C), 126.5, 126.3 (2 C), 57.9, 51.3, 50.9, 50.5, 48.1.
HRMS (ESI+): m/z [M]+ calcd for C25H23NO3: 385.1678; found: 385.1663.
#
(±)-Methyl (3R*,4R*,5R*,6R*)-3,4,6-Triphenylpyridin-2-one-5-carboxylate (6) and (±)-Methyl (3S*,4S*,5R*,6R*)-3,4,6-Triphenylpyridin-2-one-5-carboxylate (7)
Following the general procedure 3, the reaction of trans-3a (21 mg, 0.05 mmol) afforded a 1:1 mixture of compounds 6 and 7, which was separated by column chromatography (6: 10 mg, 49%, white solid) (7: 10 mg, 49%, white solid).
#
6
Mp 192–194 °C.
1H NMR (300 MHz, CDCl3): δ = 7.49 (dd, J = 7.9, 1.8 Hz, 2 H), 7.45–7.36 (m, 3 H), 7.30–7.24 (m, 3 H), 7.19 (dd, J = 6.7, 2.9 Hz, 2 H), 7.16–7.09 (m, 5 H), 5.98 (s, 1 H), 5.16 (d, J = 10.9 Hz, 1 H), 4.34 (d, J = 5.7 Hz, 1 H), 3.88 (dd, J = 5.5, 4.6 Hz, 1 H), 3.50 (dd, J = 10.9, 4.3 Hz, 1 H), 3.48 (s, 3 H).
13C NMR (75 MHz, CDCl3): δ = 170.9, 170.0, 140.4, 136.3, 135.9, 130.1 (2 C), 129.2 (2 C), 128.9 (2 C), 128.6, 128.6 (2 C), 127.9, 127.8 (2 C), 127.8 (2 C), 126.8, 55.9, 52.8, 52.2, 51.8, 50.7.
HRMS (ESI+): m/z [M]+ calcd for C25H23NO3: 385.1678; found: 385.1678.
#
7
Mp 190–193 °C.
1H NMR (300 MHz, CDCl3): δ = 7.52–7.47 (m, 2 H), 7.46–7.40 (m, 1 H), 7.25–7.15 (m, 4 H), 7.15–7.06 (m, 4 H), 6.89–6.83 (m, 2 H), 6.74–6.65 (m, 2 H), 6.17 (s, 1 H), 4.99 (d, J = 10.6 Hz, 1 H), 4.03 (d, J = 5.9 Hz, 1 H), 3.95 (dd, J = 12.0, 5.9 Hz, 1 H), 3.46 (dd, J = 11.9, 10.6 Hz, 1 H), 3.20 (s, 3 H).
13C NMR (75 MHz, CDCl3): δ = 172.0, 171.9, 129.9 (2 C), 129.8, 129.3 (2 C), 129.2, 128.2, 128.5 (2 C), 128.0 (2 C), 127.9 (2 C), 127.3, 127.2, 126.7 (2 C), 126.3, 58.0, 53.6, 51.6, 48.5, 47.7.
HRMS (ESI+): m/z [M]+ calcd for C25H23NO3 385.1678; found: 385.1669.
#
#
Conflict of Interest
The authors declare no conflict of interest.
Supporting Information
- Supporting information for this article is available online at https://doi-org.accesdistant.sorbonne-universite.fr/10.1055/a-1829-0262.
- Supporting Information
-
References
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For recent reviews, see:
For a recent review, see:
For selected references, see:
Corresponding Authors
Publication History
Received: 28 March 2022
Accepted after revision: 19 April 2022
Accepted Manuscript online:
19 April 2022
Article published online:
09 June 2022
© 2022. Thieme. All rights reserved
Georg Thieme Verlag KG
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-
References
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- 1g Fang X, Wang C.-J. Org. Biomol. Chem. 2018; 16: 2591
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- 1i Wei L, Chang X, Wang C.-J. Acc. Chem. Res. 2020; 53: 1084
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- 2b Potowski M, Bauer JO, Strohmann C, Antonchick AP, Waldmann H. Angew. Chem. Int. Ed. 2012; 51: 9512
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- 2d He Z.-L, Teng H-L, Wang C.-J. Angew. Chem. Int. Ed. 2013; 52: 2934
- 3a Teng H.-L, Yao L, Wang CJ. J. Am. Chem. Soc. 2014; 136: 4075
- 3b Liu H, Wu Y, Zhao Y, Li Z, Zhang L, Yang W, Jiang H, Jing C, Hao Y, Xiao Y, Guo H. J. Am. Chem. Soc. 2014; 136: 2625
- 4a Li Q.-J, Wei L, Wang C.-J. J. Am. Chem. Soc. 2014; 136: 8685
- 4b He L.-H, Sheong FK, Li Q.-J, Ling Z, Wang C.-J. Org. Lett. 2015; 17: 1365
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- 6 Wu Y, Qiao G, Liu H, Zhang L, Sun Z, Xiao Y, Guo H. RSC Adv. 2015; 5: 84290
- 7a Guo H, Liu H, Zhu F.-L, Na R, Jiang H, Wu Y, Zhang L, Li Z, Yu H, Wang B, Xiao Y, Hu X.-P, Wang M. Angew. Chem. Int. Ed. 2013; 52: 12641
- 7b Tong M.-C, Chen X, Tao H.-Y, Wang C.-J. Angew. Chem. Int. Ed. 2013; 52: 12377
- 8 Yuan C, Liu H, Gao Z, Zhou L, Feng Y, Xiao Y, Guo H. Org. Lett. 2015; 17: 26
- 9 Beletskaya IP, Najera C, Yus M. Chem. Soc. Rev. 2020; 49: 7101
- 10 Zhang L, Chen J.-J, Liu S.-S, Liang Y.-X, Zhao Y.-L. Adv. Synth. Catal. 2018; 360: 2172
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- 17 CCDC 2159441 (rac-4g) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures
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