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Synfacts 2008(2): 0162-0162  
DOI: 10.1055/s-2007-992450
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Catalytic Asymmetric Vinylogous Mukaiyama Aldol Reaction

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
L. V. Heumann, G. E. Keck*
University of Utah, Salt Lake City, USA
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Publication History

Publication Date:
23 January 2008 (online)

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Significance

This report from the Keck group extends their continous work with thiol ester derived silyl ketene acetals for the asymmetric aldol addition to the vinylogous aldol reaction. They use a BINOL/Ti(O-i-Pr)4 catalyst with B(OMe)3 as an additive in the presence of molecular sieves. While the exact role of B(OMe)3 and the sieves is not exactly known, the authors describe 1H NMR studies that help to understand some of the important interactions.