ASYMMETRIC-SYNTHESIS OF BETA-LACTAMS - HIGHLY DIASTEREOSELECTIVE ALKYLATION OF CHIRAL 2-CYANO ESTERS

Citation
C. Cativiela et al., ASYMMETRIC-SYNTHESIS OF BETA-LACTAMS - HIGHLY DIASTEREOSELECTIVE ALKYLATION OF CHIRAL 2-CYANO ESTERS, Journal of organic chemistry, 59(9), 1994, pp. 2497-2505
Citations number
39
Categorie Soggetti
Chemistry Inorganic & Nuclear
ISSN journal
00223263
Volume
59
Issue
9
Year of publication
1994
Pages
2497 - 2505
Database
ISI
SICI code
0022-3263(1994)59:9<2497:AOB-HD>2.0.ZU;2-Z
Abstract
Enolates derived from 10-(dicyclohexylsulfamoyl)isobornyl 2-substitute d-2-cyanoacetates were alkylated with very good yield and high diaster eoselectivity. The reduction of the resulting reaction products and su bsequent cyclization of the p-amino acids led to the corresponding bet a-lactam in high yields. This result paves the way for the development of a versatile and efficient asymmetric synthesis of enantiomerically pure (R)- and (S)-C(3)-disubstituted beta-lactams.