Enantioselective Addition of Diethylzinc to Aldehydes Catalyzed by Diastereomeric 1,4-Amino Alcohols with o-Xylylene Skeleton

Abstract

Abstract Two diastereomeric 1,4-amino alcohols with o-xylylene structure (S,R)-2 and (S,S)-3, synthesized from chiral 1,4-diol (S,S)-1, were utilized as chiral ligands for the enantioselective addition of diethylzinc to aldehydes. The stereochemical outcome of the reactions was controlled solely by the absolute configuration of the benzylic carbon bearing amino group, and both enantiomers of 1-substituted propanol were obtained with up to 98% (S) and 96% (R) enantiomeric excesses.