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Synfacts 2025; 21(01): 102
DOI: 10.1055/a-2467-5736
DOI: 10.1055/a-2467-5736
Peptide Chemistry
Synthesis of Diketopiperazines from α-Amino Amides and Diazophosphonate Ester Using Cp*Rh(III) Catalyst
Molas JC,
Poag EM,
Ellman JA *.
Yale University, New Haven, USA
Synthesis of Monodehydro-Diketopiperazines Enabled by Cp*Rh(III)-Catalyzed Amine-Directed N–H Functionalization.
Org. Lett. 2024;
26: 8527-8531
DOI: 10.1021/acs.orglett.4c03105
Synthesis of Monodehydro-Diketopiperazines Enabled by Cp*Rh(III)-Catalyzed Amine-Directed N–H Functionalization.
Org. Lett. 2024;
26: 8527-8531
DOI: 10.1021/acs.orglett.4c03105
Keywords
diketopiperazinse - α-amino amides - amine-directed N−H functionalization - Horner–Wadsworth–Emmons reaction
Significance
The 2.5-diketopiperazine skeleton is found in many natural products and bioactive compounds. The authors synthesized diketopiperazines from α-amino amides and diazophosphonate ester via Cp*Rh(III)-catalyzed amine-directed N–H functionalization.
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Comment
Various diketopiperazines were prepared from α-amino amides and diazophosphonate ester by way of this Cp*Rh(III)-catalyzed reaction. The phosphonate group was subsequently converted into the corresponding alkene by Horner–Wadsworth–Emmons reaction.
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Publication History
Article published online:
20 December 2024
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