Synthesis of Novel α-Aminophosphonates Containing Small Rings

 

 Buy Article Permissions and Reprints All articles of this category

Abstract

The synthesis of cyclopropyl- and cyclobutyl-substituted α-aminophosphonates by three-component microwave-assisted reaction of cyclopropanecarbaldehydes, benzylamine, and diethyl phosphite in the presence of cadmium iodide as catalyst has been developed.

References

• For some recent reviews, see:
• 1a Cativiela C. Diaz-de-Villegas MD. Tetrahedron: Asymmetry  2000,  11:  645 
  CrossrefSearch in Google Scholar
• 1b Brandi A. Goti A. Chem. Rev.  1998,  98:  589 
  CrossrefSearch in Google Scholar
• 1c Salaün J. Top. Curr. Chem.  2000,  207:  1 
  CrossrefSearch in Google Scholar
• 1d Komarov V. Grigorenko AO. Turov AV. Khilya VP. Russ. Chem. Rev.  2004,  73:  785 ; Chem. Abstr. 2005, 143, 78445
  CrossrefSearch in Google Scholar
• 2a Ma D. Zhu W. J. Org. Chem.  2001,  66:  348 
  CrossrefSearch in Google Scholar
• 2b de Meijere A. Ernst K. Zuck B. Brandl M. Kozhushkov SI. Tamm M. Yufit DS. Howard JAK. Labahn T. Eur. J. Org. Chem.  1999,  3105 
  Crossref
• 2c Pellicciari R. Marinozzi M. Camaioni E. Nunez M. Costantino G. Gasparini F. Giorgi G. Macchiarulo A. Subramanian N. J. Org. Chem.  2002,  67:  5497 
  CrossrefSearch in Google Scholar
• 2d Wurz RP. Charette AB. J. Org. Chem.  2004,  69:  1262 
  CrossrefSearch in Google Scholar
• 2e Oba M. Nishiyama N. Nishiyama K. Tetrahedron  2005,  61:  8456 
  CrossrefSearch in Google Scholar
• 2f Jimenez AI. Lopez P. Cativiela C. Chirality  2005,  17:  22 
  CrossrefSearch in Google Scholar
• 3a Dhawan B. Redmore D. Phosphorus Sulfur Relat. Elem.  1987,  32:  119 
  CrossrefSearch in Google Scholar
• 3b De Lombaert S. Blanchard L. Tan J. Sakane Y. Berry C. Ghai RD. Bioorg. Med. Chem. Lett.  1995,  5:  145 
  CrossrefSearch in Google Scholar
• 3c Burgess K. Kwok-Kan H. Destradi MS. Synlett  1994,  575 
  Crossref
• 3d Kafarski B. Lejczak B. Phosphorus, Sulfur Silicon Relat. Elem.  1991,  63:  193 
  CrossrefSearch in Google Scholar
• 3e Fields SC. Tetrahedron  1999,  55:  12237 
  CrossrefSearch in Google Scholar
• 3f Kleszczynska H. Sarapuk J. Cell. Mol. Biol. Lett.  2001,  6:  83 
  CrossrefSearch in Google Scholar
• 3g Hiratake J. Oda J. Biosci. Biotechnol. Biochem.  1997,  61:  211 
  CrossrefSearch in Google Scholar
• 4a Averina EB. Yashin NV. Grishin YuK. Kuznetsova TS. Zefirov NS. Synthesis  2006,  880 
• 4b Yashin NV. Averina EB. Grishin YuK. Kuznetsova TS. Zefirov NS. Synthesis  2006,  279 
• 4c Averina EB. Yashin NV. Shvorina EB. Grishin YuK. Kuznetsova TS. Vestn. Mosk. Univ., Ser. 2: Khim.  2005,  46:  314 ; Chem. Abstr. 2006, 145, 145989
  Search in Google Scholar
• 4d Yashin NV. Averina EB. Gerdov SM. Kuznetsova TS. Zefirov NS. Tetrahedron Lett.  2003,  44:  8241 
  Search in Google Scholar
• 4e Averina EB. Yashin NV. Kuznetsova TS. Zefirov NS. Vestn. Mosk. Univ., Ser. 2: Khim.  2002,  43:  246 ; Chem. Abstr.; 2002, 138: 254854
  Search in Google Scholar
• 5a Erion MD. Walsh CT. Biochemistry  1987,  26:  3417 
  CrossrefPubMedSearch in Google Scholar
• 5b Fadel A. J. Org. Chem.  1999,  64:  4953 
  CrossrefPubMedSearch in Google Scholar
• 6a Tesson N. Dorigneux B. Fadel A. Tetrahedron: Asymmetry  2002,  13:  2267 
  CrossrefPubMedSearch in Google Scholar
• 6b Fadel A. Tesson N. Tetrahedron: Asymmetry  2000,  11:  2023 
  CrossrefPubMedSearch in Google Scholar
• 6c Groth U. Lehmann L. Richter L. Schöllkopf U. Liebigs Ann. Chem.  1993,  427 
  CrossrefPubMed
• 6d Hercouet A. Le Corre M. Carboni B. Tetrahedron Lett.  2000,  41:  197 
  CrossrefPubMedSearch in Google Scholar
• 6e Yamazaki S. Takada T. Imanishi T. Moriguchi Y. Yamabe S. J. Org. Chem.  1998,  63:  5919 
  CrossrefPubMedSearch in Google Scholar
• 7a Demir AS. Tanyeli C. Sesenoglu O. Demic S. Tetrahedron Lett.  1996,  37:  407 
  CrossrefSearch in Google Scholar
• 7b Hannour S. Roumestant M.-L. Viallefont P. Riche C. Martinez J. El-Hallaoui A. Ouazzani F. Tetrahedron: Asymmetry  1998,  9:  2329 
  CrossrefSearch in Google Scholar
• 8 For review see: Cherkasov RA. Galkin VI. Russ. Chem. Rev.  1998,  67:  857 ; Chem. Abstr. 1999, 130, 139371
  CrossrefSearch in Google Scholar
• 9 Kabachnik MI. Medved TY. Dokl. Akad. Nauk SSSR  1952,  689 ; Chem. Abstr. 1953, 47, 2724b
• 10 Kabachnik MM. Ternovskaya TM. Zobnina EV. Beletskaya IP. Russ. J. Org. Chem. (Engl. Transl.)  2002,  38:  480 ; Chem. Abstr. 2002, 137, 370153
  CrossrefSearch in Google Scholar
• 11a Matveeva ED. Podrugina TA. Tishkovskaya EV. Zefirov NS. Synlett  2003,  2321 
  Crossref
• 11b Matveeva ED. Zefirov NS. Russ. J. Org. Chem. (Engl. Transl.)  2006,  42:  1237 
  CrossrefSearch in Google Scholar
• 11c Matveeva ED. Podrugina TA. Prisyajnoy MV. Zefirov NS. Russ. Chem. Bull.  2006,  55:  1209 
  CrossrefSearch in Google Scholar
• 12a Kabachnik MM. Zobnina EV. Beletskaya IP. Russ. J. Org. Chem. (Engl. Transl.)  2005,  41:  505 ; Chem. Abstr. 2006, 144, 350758
  Thieme ConnectSearch in Google Scholar
• 12b Kabachnik MM. Zobnina EV. Beletskaya IP. Synlett  2005,  1393 
  Thieme Connect
• 12c Kaboudin B. Nazari R. Tetrahedron Lett.  2001,  42:  8211 
  Thieme ConnectSearch in Google Scholar
• 12d Yadav JS. Subba Reddy BV. Madan C. Synlett  2001,  1131 
  Thieme Connect
• 13a Pavlov VY. Kabachnik MM. Zobnina EV. Timofeev VP. Konstantinov IO. Ponomarev GV. Beletskaya IP. Synlett  2003,  2193 
  Crossref
• 13b Kabachnik MM. Zobnina EV. Pavlov VY. Konstantinov IO. Beletskaya IP. Russ. Chem. Bull.  2005,  54:  262 ; Chem. Abstr. 2006, 144, 432906
  CrossrefSearch in Google Scholar
• 14 Corey EJ. Suggs JW. Tetrahedron Lett.  1975,  16:  2647 
  CrossrefSearch in Google Scholar

Due to the low intensity of signals, the assignment of signals in NMR spectra of only three minor isomers of 8e was performed.