The role of the planar chirality of iron tricarbonyl substituted homochiral amino alcohols in the asymmetric alkylation of aldehydes with diethylzinc

Homochiral amino alcohols bearing an iron tricarbonyl moiety were prepared from 2-amino-1,1-diphenylethanol derivatives 4a-d and [(3S,4S)-eta (4.7)-oc ta-4,6-dien-3-ol]Fe(CO)(3) complex 2. The addition of diethylzinc to aldehy des bearing electron donating substituents in the presence of these chiral ligands gave the alkylated products in good enantiomeric excess (up to 93% e.e.), whereas the addition to aldehydes bearing electron withdrawing subst ituents resulted in low yields and poor enantiomeric excesses. (C) 2001 Els evier Science Ltd. All rights reserved.