Asymmetric syntheses of .BETA.-amino acids by the addition of chiral amines to C=C double bonds.

Abstract

Asymmetric syntheses of β-amino acids were achieved by the addition of chiral amines, R (+)- and S (-)-α-methylbenzylamines (1b and 1c), to crotonitrile, methyl crotonate (5a), l-menthyl crotonate (5b), ethyl cinnamate (5c), and methacrylonitrile, and by the addition of benzylamine (1a) to 5b, in the range of 2-19% optical purities. Among them, the configuration of the resulting β-amino acids was same as 1b and 1c used, in the reactions with crotonitrile and 5c, but was different in the cases of 5a and 5b and methacrylonitrile.