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Synfacts 2010(8): 0919-0919  
DOI: 10.1055/s-0030-1257775
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Propargylation of Aldehydes by Copper Catalysis

Contributor(s): Mark Lautens, Stephen G. Newman
D. R. Fandrick*, K. R. Fandrick, J. T. Reeves, Z. Tan, W. Tang, A. G. Capacci, S. Rodriguez, J. J. Song, H. Lee, N. K. Yee, C. H. Senanayake
Boehringer Ingelheim Pharmaceuticals Inc., Ridgefield, USA
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Publication History

Publication Date:
22 July 2010 (online)

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Significance

Enantioselective propargylations provide direct access to chiral homopropargylic alcohols. While useful chiral allene reagents have been developed for this purpose, a general catalytic enantioselective propargylation has remained elusive. The authors present a simple copper-­catalyzed asymmetric propargylation of aldehydes using a propargyl borolane. High yields and enantioselectivies were obtained for numerous aryl ­aldehydes and a single vinyl and alkyl example.