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Synfacts 2010(5): 0545-0545  
DOI: 10.1055/s-0029-1219703
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Stereospecific Suzuki Cross-Coupling

Contributor(s): Mark Lautens, David A. Candito
A. He, J. R. Falck*
University of Texas Southwestern Medical Center, Dallas, USA
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Publication History

Publication Date:
22 April 2010 (online)

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Significance

There are many challenges associated with the use of secondary alkyl electrophiles as partners in metal-catalyzed cross-couplings. However, significant progress has been recently made in this area (see Review below). The authors report a protocol for the stereospecific Suzuki cross-coupling of alkyl α-cyano triflates. The mild reaction conditions, ready availability of the alkyl triflates in enantiomerically pure form, and the synthetic versatility provided by the cyano group are noteworthy features of this transformation.

Review: A. Rudolph, M. Lautens Angew. Chem. Int. Ed. 2009, 48, 2656-2670.