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Synfacts 2010(3): 0307-0307  
DOI: 10.1055/s-0029-1219405
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Diastereoselective Alkyne-Aldehyde Reductive Coupling

Contributor(s): Mark Lautens, David A. Candito
G.-Q. Tian, T. Kaiser, J. Yang*
Texas A&M University, College Station, USA
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Publication History

Publication Date:
18 February 2010 (online)

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Significance

The authors report on a two-step sequence of alkynylation followed by diastereo­selective alkyne-aldehyde reductive coupling for the synthesis of syn-1,3-diols. There are few reports of such reductive couplings which proceed with high levels of stereoselectivity (A. B. Bahadoor, A. Flyer, G. C. Micalizio J. Am. Chem. Soc. 2005, 127, 3694).