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

H. Ito; Y. Sasaki; M. Sawamura

doi:10.1055/s-0028-1087568

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Synfacts 2009(2): 0183-0183
DOI: 10.1055/s-0028-1087568

Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions

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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Publikationsverlauf

Publikationsdatum:
22. Januar 2009 (online)

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Significance

The CuOt-Bu/Xantphos-catalyzed formal S_N2′ 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.