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Synfacts 2009(2): 0183-0183  
DOI: 10.1055/s-0028-1087568
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Copper(I)-Catalyzed Substitution of Propargylic Carbonates with Diboron

Contributor(s): Hisashi Yamamoto, Pingfan Li
H. Ito*, Y. Sasaki, M. Sawamura*
Hokkaido University, Sapporo, Japan
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Publication History

Publication Date:
22 January 2009 (online)

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Significance

The CuOt-Bu/Xantphos-catalyzed formal SN2′ substitution reaction of optically active propagylic carbonate provides allenyl boronate with complete chirality transfer. The subsequent Lewis acid promoted addition reaction with aldehydes also proceeds in good diastereoselectivities and without loss of enantiomeric excess.