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Enantioselective synthesis of bicyclopentane-containing alcohols via asymmetric transfer hydrogenation
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Vyas, Vijyesh K., Clarkson, Guy J. and Wills, Martin (2021) Enantioselective synthesis of bicyclopentane-containing alcohols via asymmetric transfer hydrogenation. Organic Letters, 23 (8). pp. 3179-3183. doi:10.1021/acs.orglett.1c00889 ISSN 1523-7052.
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WRAP-Enantioselective-synthesis-bicyclopentane-alcohols-asymmetric-transfer-hydrogenation-2021.pdf - Accepted Version - Requires a PDF viewer. Download (1620Kb) | Preview |
Official URL: https://doi.org/10.1021/acs.orglett.1c00889
Abstract
Compounds a containing bicyclo[1.1.1]pentane (BCP) adjacent to a chiral center can be prepared with high enantiomeric excess through asymmetric transfer hydrogenation (ATH) of adjacent ketones. In the reduction step, the BCP occupies the position distant from the η6-arene of the catalyst. The reduction was applied to the synthesis of a BCP analogue of the antihistamine drug neobenodine.
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): | Hydrogenation , Bicyclic compounds -- Synthesis, Ketones | |||||||||||||||
Journal or Publication Title: | Organic Letters | |||||||||||||||
Publisher: | American Chemical Society (ACS) | |||||||||||||||
ISSN: | 1523-7052 | |||||||||||||||
Official Date: | 16 April 2021 | |||||||||||||||
Dates: |
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Volume: | 23 | |||||||||||||||
Number: | 8 | |||||||||||||||
Page Range: | pp. 3179-3183 | |||||||||||||||
DOI: | 10.1021/acs.orglett.1c00889 | |||||||||||||||
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 Organic Letters, 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 © 2021 American Chemical Society | |||||||||||||||
Description: | Crystallographic data were collected using an instrument (described in the Support-ing Information) purchased through support from Advantage West Midlands (AWM) and the European Regional Development Fund (ERDF). |
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Date of first compliant deposit: | 7 May 2021 | |||||||||||||||
Date of first compliant Open Access: | 5 April 2022 | |||||||||||||||
RIOXX Funder/Project Grant: |
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