Synfacts 2008(6): 0595-0595  
DOI: 10.1055/s-2008-1072620
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Nickel-Catalyzed Hiyama Cross-Coupling Reaction of α-Bromo Esters

Contributor(s): Hisashi Yamamoto, Cheol Hong Cheon
X. Dai, N. A. Strotman, G. C. Fu*
Massachusetts Institute of Technology, Cambridge, USA
Further Information

Publication History

Publication Date:
21 May 2008 (online)

Significance

The authors report the first catalytic asymmetric cross-couplings of α-halo carbonyl compounds with aryl metal reagents, thereby generating synthetically useful α-aryl carboxylic acid derivatives in good enantiomeric excess. Moreover, it is noted that this catalyst system could be applied to enantioselective alkenylation of α-halo esters. These esters were successfully converted into a corresponding alcohol or carboxylic acid without racemization.