Asymmetric synthesis of (+)-or (-)-2-methyloctanal via the metalloenamines of chiral alkoxy amines

AI Meyers, GS Poindexter, Z Brich

Index: Meyers,A.I. et al. Journal of Organic Chemistry, 1978 , vol. 43, p. 892 - 898

Full Text: HTML

Citation Number: 113

Abstract

An asymmetric synthesis of the title aldehyde (1) was investigated using chiral amines derived from (S)-or (R)-phenylalanine,(S)-leucine,(S)-valine, and (R)-phenylglycine (2). These amino acids were transformed into their chiral amino alcohols (3) via reduction and then alkylated with various alkyl, alkoxyalkyl, and dimethylaminoalkyl halides. The alkoxy amines (4) were treated with propionaldehyde or octanal to afford the chiral aldimines 5 ...