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Synfacts 2007(1): 0047-0047  
DOI: 10.1055/s-2006-955727
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Silylboronation of Allenes

Contributor(s): Mark Lautens, Andrew Martins
T. Ohmura, H. Taniguchi, M. Suginome*
Kyoto University, Japan
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Publication History

Publication Date:
15 December 2006 (online)

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Significance

A variety of allenes were enantio­selectively converted into chiral allyl silyl vinylboro­nate esters in the presence of a silylboronate and a Pd(0)/monodentate phosphine ligand. Yields and enantioselectivities were generally excellent. The reaction can be performed chemoselectively in the presence of an alkyne, and the versatility of the products was demonstrated by conversion into several interesting chiral cyclopentene compounds.