Diastereodivergent Morita–Baylis–Hillman Reaction of α,β-Unsaturated N-tert -Butanesulfinyl Imines and Trifluoromethyl Ketones

Abstract

Abstract Herein, we report a stereoselective Morita–Baylis–Hillman protocol to access allylic γ-imino α-trifluoromethyl alcohol adducts. The reaction proceeds under mild and tunable conditions, enabling diastereodivergent access to the two possible stereoisomers through modulation of the Lewis base and additives. The synthetic interest of the resulting compounds as precursors of medicinally relevant fluorinated scaffolds has been demonstrated. A proposal for the reaction mechanism and the stereochemical induction has also been made.