Sc(III)-Catalyzed Vinylsilane Addition toN-Phenylglyoxamide

Significance

In the presence of a Sc(III)/nor­ephedrinepybox catalyst system, a variety of vinylsilanes were added selectively to N-phenylglyox­amide to afford chiral allylic alcohol products in moderate to excellent yield, and with excellent enantioselectivity. When aromatic vinylsilanes are used, E-allylic alcohols are obtained exclusively, whereas alkyl-substituted vinylsilanes show retention of the alkene geometry. When R² and R³ are alkyl groups, an isomerized homoallylic alcohol is observed if no external base is added. In addition, it was also shown that the reaction with (trimethyl­silyl)phenylacetylene as nucleophile can afford a chiral propargylic alcohol with good enantioselectivity.