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Synfacts 2007(11): 1171-1171  
DOI: 10.1055/s-2007-991263
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantio- and Diastereoselective Carbonyl Addition of Propargylsilanes

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
D. A. Evans*, Y. Aye
Harvard University, Cambridge, USA
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Publication History

Publication Date:
23 October 2007 (online)

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Significance

The Evans group has developed a propargylsilane addition to N-phenylglyoxamide catalyzed by an aluminum Lewis acid. High yields and enantioselectivities were obtained for a variety of substrates. The conditions tolerate remote olefinic substitution as well as a silylated alcohol. The vinyl epoxide products are very useful compounds that are suitable for a variety of transformations.