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Asymmetric Alkyl−Alkyl Cross-Couplings of Unactivated Secondary Alkyl Electrophiles: Stereoconvergent Suzuki Reactions of Racemic Acylated Halohydrins

Owston, Nathan A. and Fu, Gregory C. (2010) Asymmetric Alkyl−Alkyl Cross-Couplings of Unactivated Secondary Alkyl Electrophiles: Stereoconvergent Suzuki Reactions of Racemic Acylated Halohydrins. Journal of the American Chemical Society, 132 (34). pp. 11908-11909. ISSN 0002-7863. PMCID PMC2929007. https://resolver.caltech.edu/CaltechAUTHORS:20200428-095146269

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Abstract

A method for asymmetric alkyl−alkyl Suzuki reactions of unactivated secondary alkyl electrophiles, specifically, cross-couplings of racemic acylated halohydrins with alkylborane reagents, has been developed. A range of protected bromohydrins, as well as a protected chlorohydrin and a homologated bromohydrin, are coupled in good ee by a catalyst derived from commercially available components.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/ja105924fDOIArticle
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2929007/PubMed CentralArticle
ORCID:
AuthorORCID
Fu, Gregory C.0000-0002-0927-680X
Additional Information:© 2010 American Chemical Society. Received July 5, 2010. We thank Angelika Bruckmann for preliminary studies. Support has been provided by the National Institutes of Health (National Institute of General Medical Sciences, Grant R01-GM62871).
Funders:
Funding AgencyGrant Number
NIHR01-GM62871
Issue or Number:34
PubMed Central ID:PMC2929007
Record Number:CaltechAUTHORS:20200428-095146269
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20200428-095146269
Official Citation:Asymmetric Alkyl−Alkyl Cross-Couplings of Unactivated Secondary Alkyl Electrophiles: Stereoconvergent Suzuki Reactions of Racemic Acylated Halohydrins Nathan A. Owston and Gregory C. Fu Journal of the American Chemical Society 2010 132 (34), 11908-11909 DOI: 10.1021/ja105924f
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:102858
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:29 Apr 2020 17:23
Last Modified:29 Apr 2020 17:23

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