Asymmetric Suzuki Cross-Couplings of Activated Secondary Alkyl Electrophiles: Arylations of Racemic α-Chloroamides
Name
Fu_Asymmetric suzuki.pdf
Size
481.18 KB
Format
Adobe PDF
Checksum (MD5)
d7edb978248f53c9ee8ae1e7c1aae2a8
Author(s)
Lundin, Pamela M.
Fu, Gregory C.
Date Issued
August 2010
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
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.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
Terms of Use
Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use.
Persistent DSpace Link
DOI of Published Version
https://doi.org/10.1021/ja105148g
