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Isothiourea‐catalyzed acylative kinetic resolution of tertiary α‐Hydroxy esters
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Qu, Shen, Smith, Sam, Laina, Victor, Neyyappadath, Rifahath M., Greenhalgh, Mark D. and Smith, Andrew David (2020) Isothiourea‐catalyzed acylative kinetic resolution of tertiary α‐Hydroxy esters. Angewandte Chemie International Edition, 59 (38). pp. 16572-16578. doi:10.1002/anie.202004354 ISSN 1433-7851.
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WRAP-Isothiourea‐catalyzed-acylative-kinetic-tertiary‐Hydroxy-Greenhalgh-2020.pdf - Accepted Version - Requires a PDF viewer. Download (1768Kb) | Preview |
Official URL: http://dx.doi.org/10.1002/anie.202004354
Abstract
A highly enantioselective isothiourea‐catalyzed acylative kinetic resolution (KR) of acyclic tertiary alcohols has been developed. Selectivity factors of up to 200 were achieved for the KR of tertiary alcohols bearing an adjacent ester substituent, with both reaction conversion and enantioselectivity found to be sensitive to the steric and electronic environment at the stereogenic tertiary carbinol centre. For more sterically‐congested alcohols, the use of a recently‐developed isoselenourea catalyst was optimal, with equivalent enantioselectivity but higher conversion achieved in comparison to the isothiourea HyperBTM. Diastereomeric acylation transition state models are proposed to rationalize the origins of enantiodiscrimination in this process. This KR procedure has also been translated to a continuous flow process using a polymer‐supported variant of the catalyst.
Item Type: | Journal Article | ||||||||
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Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||||||
Journal or Publication Title: | Angewandte Chemie International Edition | ||||||||
Publisher: | Wiley - V C H Verlag GmbH & Co. KGaA | ||||||||
ISSN: | 1433-7851 | ||||||||
Official Date: | 14 September 2020 | ||||||||
Dates: |
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Volume: | 59 | ||||||||
Number: | 38 | ||||||||
Page Range: | pp. 16572-16578 | ||||||||
DOI: | 10.1002/anie.202004354 | ||||||||
Status: | Peer Reviewed | ||||||||
Publication Status: | Published | ||||||||
Reuse Statement (publisher, data, author rights): | "This is the peer reviewed version of the following article: Qu, S., Smith, S., Laina, V., Neyyappadath, R..M., Greenhalgh, M. and Smith, A..D. (2020), Isothiourea‐Catalyzed Acylative Kinetic Resolution of Tertiary α‐Hydroxy Esters. Angew. Chem. Int. Ed.. Accepted Author Manuscript. doi:10.1002/anie.202004354 , which has been published in final form at http://dx.doi.org/10.1002/anie.202004354 . This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions." | ||||||||
Access rights to Published version: | Open Access (Creative Commons) | ||||||||
Date of first compliant deposit: | 16 June 2020 | ||||||||
Date of first compliant Open Access: | 3 June 2021 | ||||||||
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