Diastereoselective addition of lithiated N,N-diethyl-o-toluamide to chiral isopropylidine glyceraldehyde lmines. Asymmetric synthesis of 3-substituted 3,4-dihydro-1(2H)-isoquinolones

Abstract

The lithio derivative of N,N-diethyl-o-toluamide adds regiospecifically to (R)-and (S)-glyceraldehyde acetonide p-methoxybenzyl imines to afford the Cram-chelation controlled products (3S,1′R)-(3) and (3R,1′S)-(3),respectively.