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Synfacts 2010(11): 1277-1277  
DOI: 10.1055/s-0030-1258798
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Suzuki Cross-Coupling of Secondary Alkyl Electrophiles

Contributor(s): Mark Lautens, Jane Panteleev
P. M. Lundin, G. C. Fu*
Massachusetts Institute of Technology, Cambridge, USA
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Publication History

Publication Date:
21 October 2010 (online)

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Significance

A stereoconvergent asymmetric Suzuki coupling of racemic α-chloroamides and Ar-(9-BBN) is reported. The group’s earlier work on the Negishi, Hiyama, and Kumada coupling of α-bromoketones paved the way for this work. There are few examples of Suzuki couplings forming either alkyl-alkyl or aryl-aryl bonds enantio­selectively, and this is the first example of an ­enantioselective Suzuki coupling of an aryl-boron reagent with activated alkyl-halide electrophiles.

Reviews: F. Glorius Angew. Chem. Int. Ed. 2008, 47, 8347-8349; A. Rudolph, M. Lautens Angew. Chem. Int. Ed. 2009, 48, 2656-2670.