ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO PHOSPHONIC-ACIDS BY DIASTEREOSELECTIVE ADDITION OF TRIMETHYL PHOSPHITE ONTO CHIRAL OXAZOLIDINES

Citation
C. Maury et al., ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO PHOSPHONIC-ACIDS BY DIASTEREOSELECTIVE ADDITION OF TRIMETHYL PHOSPHITE ONTO CHIRAL OXAZOLIDINES, Journal of organic chemistry, 61(11), 1996, pp. 3687-3693
Citations number
46
Categorie Soggetti
Chemistry Inorganic & Nuclear
ISSN journal
00223263
Volume
61
Issue
11
Year of publication
1996
Pages
3687 - 3693
Database
ISI
SICI code
0022-3263(1996)61:11<3687:AOAPBD>2.0.ZU;2-F
Abstract
A simple and general asymmetric synthesis of alpha-amino phosphonic ac ids is described. The method involves the highly selective addition of trialkyl phosphite onto various chiral oxazolidines. Oxazaphosphorina nes thus obtained with an excellent diastereoselectivity furnish the c orresponding (S)-alpha-substituted amino phosphonic acids in good over all yields and high ee (77-->97%) after simple deprotection.