Asymmetric Hydrocyanation of Aldehydes Using Chiral Titanium Reagents

Abstract

Two highly enantioselective methods for hydrocyanation of aldehydes were developed by using chiral alkoxytitanium reagents. Treatment of benzaldehyde with cyanotrimethylsilane in the presence of a chiral alkoxytitanium affords mandelonitrile in good chemical and optical yields. By the use of the chiral cyanotitanium reagent generated in situ from the chiral alkoxytitanium and cyanotrimethylsilane, aliphatic aldehydes are converted into the corresponding cyanohydrins in a highly enantioselective manner.