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A C=O⋅⋅⋅Isothiouronium interaction dictates enantiodiscrimination in acylative kinetic resolutions of tertiary heterocyclic alcohols
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Greenhalgh, Mark D., Smith, Samuel M, Walden, Daniel M., Taylor, James E., Brice, Zamira, Robinson, Emily R. T., Fallan, Charlene, Cordes, David B., Slawin, Alexandra M. Z., Richardson, H. Camille, Grove, Markas A., Cheong, Paul Ha-Yeon and Smith, Andrew D. (2018) A C=O⋅⋅⋅Isothiouronium interaction dictates enantiodiscrimination in acylative kinetic resolutions of tertiary heterocyclic alcohols. Angewandte Chemie-International Edition, 57 (12). pp. 3200-3206. doi:10.1002/anie.201712456 ISSN 1433-7851.
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Official URL: https://doi.org/10.1002/anie.201712456
Abstract
A combination of experimental and computational studies have identified a C=O⋅⋅⋅isothiouronium interaction as key to efficient enantiodiscrimination in the kinetic resolution of tertiary heterocyclic alcohols bearing up to three potential recognition motifs at the stereogenic tertiary carbinol center. This discrimination was exploited in the isothiourea-catalyzed acylative kinetic resolution of tertiary heterocyclic alcohols (38 examples, s factors up to >200). The reaction proceeds at low catalyst loadings (generally 1 mol %) with either isobutyric or acetic anhydride as the acylating agent under mild conditions.
Item Type: | Journal Article | |||||||||||||||||||||
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Subjects: | Q Science > QD Chemistry | |||||||||||||||||||||
Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | |||||||||||||||||||||
Library of Congress Subject Headings (LCSH): | Chemical kinetics, Lewis acids, Acylation | |||||||||||||||||||||
Journal or Publication Title: | Angewandte Chemie-International Edition | |||||||||||||||||||||
Publisher: | Wiley-Blackwell Publishing | |||||||||||||||||||||
ISSN: | 1433-7851 | |||||||||||||||||||||
Official Date: | 12 March 2018 | |||||||||||||||||||||
Dates: |
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Volume: | 57 | |||||||||||||||||||||
Number: | 12 | |||||||||||||||||||||
Page Range: | pp. 3200-3206 | |||||||||||||||||||||
DOI: | 10.1002/anie.201712456 | |||||||||||||||||||||
Status: | Peer Reviewed | |||||||||||||||||||||
Publication Status: | Published | |||||||||||||||||||||
Reuse Statement (publisher, data, author rights): | "This is the peer reviewed version of the following article: M. D. Greenhalgh, S. M. Smith, D. M. Walden, J. E. Taylor, Z. Brice, E. R. T. Robinson, C. Fallan, D. B. Cordes, A. M. Z. Slawin, H. C. Richardson, M. A. Grove, P. H.-Y. Cheong, A. D. Smith, Angew. Chem. Int. Ed. 2018 , 57 , 3200, which has been published in final form at https://doi.org/10.1002/anie.201712456. 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: | Restricted or Subscription Access | |||||||||||||||||||||
Date of first compliant deposit: | 14 May 2020 | |||||||||||||||||||||
Date of first compliant Open Access: | 26 May 2020 | |||||||||||||||||||||
Grant number: | EPSRC Grant Number: EP/J500549/1; ERC Grant Number: 279850; National Science Foundation Grant Numbers: CHE-1352663, CHE-1102637 | |||||||||||||||||||||
RIOXX Funder/Project Grant: |
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