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Asymmetric transfer hydrogenation : dynamic kinetic resolution of α-amino ketones
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Gediya, Shweta, Clarkson, Guy J. and Wills, Martin (2020) Asymmetric transfer hydrogenation : dynamic kinetic resolution of α-amino ketones. The Journal of Organic Chemistry, 85 (17). pp. 11309-11330. doi:10.1021/acs.joc.0c01438 ISSN 1520-6904.
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WRAP-Asymmetric-transfer-hydrogenation-dynamic-kinetic-resolution-Wills-2020.pdf - Accepted Version - Requires a PDF viewer. Download (2351Kb) | Preview |
Official URL: https://doi.org/10.1021/acs.joc.0c01438
Abstract
A series of α-amino ketones were reduced using asymmetric transfer hydrogenation (ATH) through a dynamic kinetic resolution (DKR). The protecting group was matched to the reducing agent and following optimization, a series of substrates were investigated, giving products in high diastereoselectivity, over 99% ee in several cases and full conversion. The methodology was applied to the enantioselective synthesis of a MDM2–p53 inhibitor precursor.
Item Type: | Journal Article | |||||||||
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Subjects: | Q Science > QD Chemistry | |||||||||
Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | |||||||||
SWORD Depositor: | Library Publications Router | |||||||||
Library of Congress Subject Headings (LCSH): | Chemistry, Organic | |||||||||
Journal or Publication Title: | The Journal of Organic Chemistry | |||||||||
Publisher: | American Chemical Society (ACS) | |||||||||
ISSN: | 1520-6904 | |||||||||
Official Date: | 4 September 2020 | |||||||||
Dates: |
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Volume: | 85 | |||||||||
Number: | 17 | |||||||||
Page Range: | pp. 11309-11330 | |||||||||
DOI: | 10.1021/acs.joc.0c01438 | |||||||||
Status: | Peer Reviewed | |||||||||
Publication Status: | Published | |||||||||
Reuse Statement (publisher, data, author rights): | “This document is the Accepted Manuscript version of a Published Work that appeared in final form in The Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see [insert ACS Articles on Request author-directed link to Published Work, see http://pubs.acs.org/page/policy/articlesonrequest/index.html].” | |||||||||
Access rights to Published version: | Restricted or Subscription Access | |||||||||
Copyright Holders: | Copyright © 2020 American Chemical Society | |||||||||
Date of first compliant deposit: | 2 September 2020 | |||||||||
Date of first compliant Open Access: | 7 August 2021 | |||||||||
RIOXX Funder/Project Grant: |
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