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

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 LiBHEt3 and Catecholborane provides CF3-substituted syn- and anti-1,3-amino alcohols 5a and 5b in high yields with excellent diastereoselectivities (dr > 99:1).

Graphical abstractRegiospecific 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).Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Regiospecific and diastereoselective aldol type reaction of chiral N-sulfinyl metalloenamines with α,β-unsaturated trifluoromethyl ketones is described. ► The reaction tolerates a wide range of N-(tert-butanesulfinyl) ketimines and α,β-unsaturated trifluoromethyl ketones. ► The reaction provides a practical method for the asymmetric synthesis of tertiary trifluoromethyl allylic carbinols with good diastereoselectivities.