The Role of the Planar Chirality of Iron Tricarbonyl Substituted Homochiral Amino Alcohols in the Asymmetric Alkylation of Aldehydes with Diethylzinc.

Abstract Homochiral amino alcohols bearing an iron tricarbonyl moiety were prepared from 2-amino-1,1-diphenylethanol derivatives 4a–d and [(3S,4S)-η4,7-octa-4,6-dien-3-ol]Fe(CO)3 complex 2. The addition of diethylzinc to aldehydes 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 substituents resulted in low yields and poor enantiomeric excesses.