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Synfacts 2010(7): 0795-0795
DOI: 10.1055/s-0029-1220085
DOI: 10.1055/s-0029-1220085
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Asymmetric Conjugate Additions of 3-Boronyl Unsaturated Esters
J. C. H. Lee, D. G. Hall*
University of Alberta, Edmonton, Canada
Further Information
Publication History
Publication Date:
22 June 2010 (online)
Significance
Organoboron reagents are extremely useful in organic synthesis due to the ability to functionalize the B-C bond. These functionalizations typically proceed with retention of stereochemistry at the carbon-bearing boron. With the advent of stereospecific cross-couplings of organoboron reagents, there is an increasing push to generate these reagents as single enantiomers. The authors report a conceptually different approach in which a copper-catalyzed asymmetric conjugate addition is preformed on a 3-boronyl unsaturated ester. This method expands the scope of available chiral boron reagents via a novel strategy.