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Scope, limitations and mechanistic analysis of the HyperBTM‐catalyzed acylative kinetic resolution of tertiary heterocyclic alcohols
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Smith, Samuel M., Greenhalgh, Mark D., Feoktistova, Taisiia, Walden, Daniel M., Taylor, James E., Cordes, David B., Slawin, Alexandra M. Z., Cheong, Paul Ha‐Yeon and Smith, Andrew D. (2022) Scope, limitations and mechanistic analysis of the HyperBTM‐catalyzed acylative kinetic resolution of tertiary heterocyclic alcohols. European Journal of Organic Chemistry, 2022 (1). e00264. doi:10.1002/ejoc.202101111 ISSN 1434-193X.
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WRAP-Scope-limitations-mechanistic-analysis-HyperBTM-catalyzed-kinetic-tertiary-heterocyclic-alcohols-2021.pdf - Accepted Version - Requires a PDF viewer. Download (2552Kb) | Preview |
Official URL: http://dx.doi.org/10.1002/ejoc.202101111
Abstract
The full scope and limitations of the catalytic acylative kinetic resolution of a range of tertiary heterocyclic alcohols (78 examples, s up to >200) is reported under operationally-simple conditions, using low loadings of a commercially available Lewis basic isothiourea catalyst, HyperBTM (generally 1 mol %). The protocol is highly effective for the kinetic resolution of 3-substituted 3-hydroxyoxindole and α-substituted α-hydroxylactam derivatives bearing up to three potential recognition motifs at the stereogenic tertiary carbinol center. The full power of this methodology has been showcased through the synthesis of highly enantioenriched biologically-active target compounds in both enantiomeric forms. To provide further insight into the reaction mechanism, a detailed kinetic analysis of this Lewis base-catalyzed acylation of tertiary alcohols is reported using the variable time normalization analysis (VTNA) method.
Item Type: | Journal Article | ||||||||||
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Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||||||||
Journal or Publication Title: | European Journal of Organic Chemistry | ||||||||||
Publisher: | Wiley | ||||||||||
ISSN: | 1434-193X | ||||||||||
Official Date: | 11 January 2022 | ||||||||||
Dates: |
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Volume: | 2022 | ||||||||||
Number: | 1 | ||||||||||
Article Number: | e00264 | ||||||||||
DOI: | 10.1002/ejoc.202101111 | ||||||||||
Status: | Peer Reviewed | ||||||||||
Publication Status: | Published | ||||||||||
Reuse Statement (publisher, data, author rights): | "This is the peer reviewed version of the following article: Smith, S.M., Greenhalgh, M.D., Feoktistova, T., Walden, D.M., Taylor, J.E., Cordes, D.B., Slawin, A.M.Z., Cheong, P.H.-Y. and Smith, A.D. (2021), Scope, Limitations and Mechanistic Analysis of the HyperBTM-Catalyzed Acylative Kinetic Resolution of Tertiary Heterocyclic Alcohols** . Eur. J. Org. Chem.. https://doi.org/10.1002/ejoc.202101111, which has been published in final form at https://doi.org/10.1002/ejoc.202101111. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited." | ||||||||||
Access rights to Published version: | Open Access (Creative Commons) | ||||||||||
Description: | Free to read |
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Date of first compliant deposit: | 29 November 2021 | ||||||||||
Date of first compliant Open Access: | 4 October 2023 |
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