Regiospecific and diastereoselective aldol reaction of chiral N-sulfinyl metalloenamines with α,β-unsaturated trifluoromethyl ketones: Asymmetric synthesis of tertiary trifluoromethyl allylic carbinols

Abstract Regiospecific and diastereoselective aldol type reaction of chiral N -sulfinyl metalloenamines with α,β-unsaturated trifluoromethyl ketones was reported, which affords the corresponding tertiary trifluoromethyl allylic carbinols in high yields with good diastereoselectivities (dr up to 90:10). The reduction of the condensation product 3a with LiBHEt 3 and Catecholborane provides CF 3 -substituted syn - and anti -1,3-amino alcohols 5a and 5b in high yields with excellent diastereoselectivities (dr > 99:1).