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Asymmetric Suzuki Cross-Couplings of Activated Secondary Alkyl Electrophiles: Arylations of Racemic α-Chloroamides

Author(s)
Lundin, Pamela M.; Fu, Gregory C.
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Abstract
A nickel-catalyzed stereoconvergent method for the enantioselective Suzuki arylation of racemic α-chloroamides has been developed. This process provides a unique example of an asymmetric arylation of an α-haloamide, an enantioselective arylation of an α-chlorocarbonyl compound, and an asymmetric Suzuki reaction with an activated alkyl electrophile or an arylboron reagent. The method is also applicable to the corresponding enantioselective cross-coupling of α-bromoamides. The coupling products can be transformed without racemization into enantioenriched α-arylcarboxylic acids and primary alcohols. A modest kinetic resolution of the α-chloroamide was observed; a mechanistic study indicated that the selectivity may reflect discrimination by the chiral catalyst of the two enantiomeric α-chloroamides in an irreversible oxidative-addition process.
Date issued
2010-08
URI
http://hdl.handle.net/1721.1/82114
Department
Massachusetts Institute of Technology. Department of Chemistry
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society
Citation
Lundin, Pamela M., and Gregory C. Fu. “Asymmetric Suzuki Cross-Couplings of Activated Secondary Alkyl Electrophiles: Arylations of Racemic α-Chloroamides.” Journal of the American Chemical Society 132, no. 32 (August 18, 2010): 11027-11029.
Version: Author's final manuscript
ISSN
0002-7863
1520-5126

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