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Convergent Catalytic Asymmetric Synthesis of Esters of Chiral Dialkyl Carbinols

Yang, Ze-Peng and Fu, Gregory C. (2020) Convergent Catalytic Asymmetric Synthesis of Esters of Chiral Dialkyl Carbinols. Journal of the American Chemical Society, 142 (12). pp. 5870-5875. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20200316-151135011

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Abstract

Because chiral dialkyl carbinols, as well as their derived esters, are significant as intermediates and end points in fields such as organic, pharmaceutical, and biological chemistry, the development of efficient approaches to their asymmetric synthesis is an important endeavor. In this report, we describe a method for the direct catalytic enantioselective synthesis of such esters, beginning with an alkyl halide (derived from an aldehyde and an acyl bromide), an olefin, and a hydrosilane, catalyzed by nickel, an earth-abundant metal. The method is versatile, tolerating substituents that vary in size and that bear a range of functional groups. We further describe a four-component variant of this process, wherein the alkyl halide is generated in situ, thus obviating the need to isolate either an alkyl electrophile or an alkylmetal, while still effecting an alkyl–alkyl coupling. Finally, we apply our convergent method to the efficient catalytic enantioselective synthesis of three esters that are bioactive themselves or that have been utilized in the synthesis of bioactive compounds.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/jacs.0c01324DOIArticle
ORCID:
AuthorORCID
Yang, Ze-Peng0000-0003-0248-1963
Fu, Gregory C.0000-0002-0927-680X
Additional Information:© 2020 American Chemical Society. Received: February 3, 2020; Published: March 16, 2020. Support was provided by the National Institutes of Health (National Institute of General Medical Sciences; grant R01-GM062871), the Shanghai Institute of Organic Chemistry (fellowship to Z.-P.Y.), and the Dow Next-Generation Educator Fund (grant to Caltech). We thank Dr. Caiyou Chen, Dr. Haohua Huo, Dr. Paul H. Oyala, Dr. David G. VanderVelde, Dr. Scott C. Virgil, and Dr. Zhaobin Wang for assistance and for helpful discussions. The authors declare no competing financial interest.
Funders:
Funding AgencyGrant Number
NIHR01-GM062871
Shanghai Institute of Organic Chemistry (SIOC)UNSPECIFIED
Dow Next-Generation Education FundUNSPECIFIED
Issue or Number:12
Record Number:CaltechAUTHORS:20200316-151135011
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20200316-151135011
Official Citation:Convergent Catalytic Asymmetric Synthesis of Esters of Chiral Dialkyl Carbinols. Ze-Peng Yang and Gregory C. Fu. Journal of the American Chemical Society 2020 142 (12), 5870-5875; DOI: 10.1021/jacs.0c01324
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:101936
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:17 Mar 2020 14:38
Last Modified:25 Mar 2020 15:36

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