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

Lundin, Pamela M. and Fu, Gregory C. (2010) Asymmetric Suzuki Cross-Couplings of Activated Secondary Alkyl Electrophiles: Arylations of Racemic α-Chloroamides. Journal of the American Chemical Society, 132 (32). pp. 11027-11029. ISSN 0002-7863. PMCID PMC2924160. https://resolver.caltech.edu/CaltechAUTHORS:20200428-095146364

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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.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/ja105148gDOIArticle
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2924160/PubMed CentralArticle
ORCID:
AuthorORCID
Fu, Gregory C.0000-0002-0927-680X
Additional Information:© 2010 American Chemical Society. Received June 12, 2010. We thank Dr. Francisco González-Bobes for preliminary studies. Support was provided by the National Institutes of Health (National Institute of General Medical Sciences, Grant R01-GM62871), Eli Lilly (fellowship to P.M.L.), Novartis (fellowship to P.M.L.), and the Merck Research Laboratories.
Funders:
Funding AgencyGrant Number
NIHR01-GM62871
Eli LillyUNSPECIFIED
NovartisUNSPECIFIED
Merck Research LaboratoriesUNSPECIFIED
Issue or Number:32
PubMed Central ID:PMC2924160
Record Number:CaltechAUTHORS:20200428-095146364
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20200428-095146364
Official Citation:Asymmetric Suzuki Cross-Couplings of Activated Secondary Alkyl Electrophiles: Arylations of Racemic α-Chloroamides Pamela M. Lundin and Gregory C. Fu Journal of the American Chemical Society 2010 132 (32), 11027-11029 DOI: 10.1021/ja105148g
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:102859
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:29 Apr 2020 19:02
Last Modified:29 Apr 2020 19:02

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