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Synfacts 2010(12): 1388-1388
DOI: 10.1055/s-0030-1258895
DOI: 10.1055/s-0030-1258895
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Reductive Enolization in Aldol Addition to Enolizable Aldehydes
S. J. Sauer, M. R. Garnsey, D. M. Coltart*
Duke University, Durham, USA
Further Information
Publication History
Publication Date:
22 November 2010 (online)
Significance
The authors report a new strategy toward forming aldol adducts in the presence of enolizable aldehydes, which relies on forming enolates by a magnesium-promoted reduction of α-halo thioesters with Ph3P. This strategy offers a mild alternative to the traditional stepwise LDA-mediated protocol required for high chemoselectivity in classical aldol additions. The high syn diastereoselectivity of this reaction is complementary to the LDA-mediated protocols.