Stereoselective synthesis of racemic α-amino-acid derivatives with a β-lactam skeleton: Application of the Staudinger reaction to chiral imines of methyl glyoxylate

Article abstract of DOI:10.1016/S0040-4020(98)00683-8

Selected imines of methyl glyoxylate act as good partners in the Staudinger cycloaddition reaction with a series of substituted ketenes. The cis stereoselectivity is almost complete with electron-donor substituted ketenes, but the asymmetric induction is low when imines derived from chiral l-aryl-ethylamines are used.