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DOI: 10.1055/s-2006-949440
Sc(III)-Catalyzed Vinylsilane Addition toN-Phenylglyoxamide
D. A. Evans*, Y. Aye
Harvard University, Cambridge, USA
Publication History
Publication Date:
24 October 2006 (online)

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.