Electrogenerated cyanomethyl anion in organic synthesis: A simple diastereoselective synthesis of cis-3-alkyl-1-benzyl-4-ethoxycarbonyl-β- lactams

Tetrahedron Letters

Volumn 46, Issue 49, 2005, Pages 8517-8519

  Feroci, Marta ^a   Lessard, Jean ^b   Orsini, Monica ^a   Inesi, Achille ^c  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b UNIVERSITÉ DE SHERBROOKE   (Canada)

^c UNIVERSITY OF L'AQUILA   (Italy)

Author keywords

Lactams; Cathodic reduction; Electrogenerated cyanomethyl anion; Electrosynthesis

Indexed keywords

AMIDE; BETA LACTAM DERIVATIVE;

ADDITION REACTION; ARTICLE; CIS ISOMER; DIASTEREOISOMER; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTROCHEMISTRY; ELECTROLYSIS; ISOMERIZATION; STEREOCHEMISTRY; STRUCTURE ANALYSIS; TRANS ISOMER;

EID: 27644593861     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.10.008     Document Type: Article

References (17)

1. M.I. Page The Chemistry of β-Lactams 1992 Blackie Academic & Professional New York
2. G.I. Georg The Organic Chemistry of β-Lactams 1993 VCH Press New York
3. R.B. Morin M. Gorman Chemistry and Biology of β-Lactam Antibiotics Vols. 1-3 1982 Academic Press New York
4. B. Alcaide, P. Almendros, J.M. Alonso, and M.C. Redondo J. Org. Chem. 68 2003 1426 and references cited therein
5. A.H. Berks Tetrahedron 52 1996 331 and references cited therein
6. G.S. Singh Tetrahedron 59 2003 7631
7. C. Palomo, J.M. Aizpurua, I. Ganboa, and M. Oiarbide Eur. J. Org. Chem. 1999 3223
8. D.J. Hart, and D.-C. Ha Chem. Rev. 89 1989 1447
9. M.A. Casadei, A. Inesi, F. Micheletti Moracci, and D. Occhialini Tetrahedron 44 1988 2601
10. As regards electrogenerated bases, see: M.M. Baizer H. Lund M.M. Baizer Organic Electrochemistry 1991 Marcel Dekker Inc. NewYork 1265 1282 and references cited therein
11. I. Carelli, A. Inesi, V. Carelli, M.A. Casadei, F. Liberatore, and F. Micheletti Moracci Synthesis 7 1986 591
12. M.A. Casadei, A. Gessner, A. Inesi, W. Jugelt, H. Liebezeit, and F. Micheletti Moracci Bull. Soc. Chim. Fr. 125 1989 650
13. L. Rossi, M. Feroci, and A. Inesi Mini-Rev. Org. Chem. 2 2005 343 357
14. M. Feroci, M. Orsini, L. Palombi, L. Rossi, and A. Inesi Electrochim. Acta 50 2005 2029 and references cited therein
15. 3: C, 69.79; H, 7.69, N, 5.09. Found: C, 69.15; H, 8.09; N, 4.80.
16. 2CN induced cyclization of 2-bromocarboxamides), the reactivity of 1c versus a classical organic base has been carried out (LDA in THF, -78°C). β-Lactam 2c was not isolated and 1c was quantitatively recovered. See also Ref. 9.
17. T. Kawabata, T. Minami, and T. Hiyama J. Org. Chem. 57 1992 1864