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
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.