Enantioselective Scandium-Catalyzed Vinylsilane Additions:A New Approach to the Synthesis of Enantiopure beta,gamma-Unsaturated alpha-Hydroxy Acid Derivatives

摘要

The purpose of this study is to report the enantioselective Lewis acid-promoted addition of vinylsilanes to N-phenylglyoxamide 2 catalyzed by the chiral Sc(III)complex 1f(eq 1).Carbonyl addition reactions of vinylsilane nucleophiles are rare,presumably due to the low intrinsic nucleophilicity associated with these organosilicon reagents.Intramolecular vinylsilane additions to iminium ions have been reported;however,to our knowledge,the present examples represent the first intermolecular Lewis acid-catalyzed vinylsilane addition reactions.