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Horeau amplification in the sequential acylative kinetic resolution of (±)-1,2-diols and (±)-1,3-diols in flow
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Brandolese, Arianna, Greenhalgh, Mark D., Desrues, Titouan, Liu, Xueyang, Qu, Shen, Bressy, Cyril and Smith, Andrew D. (2021) Horeau amplification in the sequential acylative kinetic resolution of (±)-1,2-diols and (±)-1,3-diols in flow. Organic & Biomolecular Chemistry, 19 (16). pp. 3620-3627. doi:10.1039/d1ob00304f
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WRAP-Horeau-amplification-sequential-acylative-kinetic-resolution-Greenhalgh-2021.pdf - Published Version - Requires a PDF viewer. Available under License Creative Commons Attribution. Download (3441Kb) | Preview |
Official URL: https://doi.org/10.1039/d1ob00304f
Abstract
The sequential acylative kinetic resolution (KR) of C2-symmetric (±)-1,2-syn and (±)-1,3-anti-diols using a packed bed microreactor loaded with the polystyrene-supported isothiourea, HyperBTM, is demonstrated in flow. The sequential KRs of C2-symmetric (±)-1,2-syn and (±)-1,3-anti-diols exploits Horeau amplification, with each composed of two successive KR processes, with each substrate class significantly differing in the relative rate constants for each KR process. Optimisation of the continuous flow set-up for both C2-symmetric (±)-1,2-syn and (±)-1,3-anti-diol substrate classes allowed isolation of reaction products in both high enantiopurity and yield. In addition to the successful KR of C2-symmetric (±)-1,2-syn and (±)-1,3-anti-diols, the application of this process to the more conceptually-complex scenario involving the sequential KR of C1-symmetric (±)-1,3-anti-diols was demonstrated, which involves eight independent rate constants.
| Item Type: | Journal Article | |||||||||||||||||||||
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| Subjects: | Q Science > QD Chemistry T Technology > TR Photography |
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| Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | |||||||||||||||||||||
| SWORD Depositor: | Library Publications Router | |||||||||||||||||||||
| Library of Congress Subject Headings (LCSH): | Chemical kinetics, Microreactors , Glycols | |||||||||||||||||||||
| Journal or Publication Title: | Organic & Biomolecular Chemistry | |||||||||||||||||||||
| Publisher: | Royal Society of Chemistry | |||||||||||||||||||||
| ISSN: | 1477-0520 | |||||||||||||||||||||
| Official Date: | 2021 | |||||||||||||||||||||
| Dates: |
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| Volume: | 19 | |||||||||||||||||||||
| Number: | 16 | |||||||||||||||||||||
| Page Range: | pp. 3620-3627 | |||||||||||||||||||||
| DOI: | 10.1039/d1ob00304f | |||||||||||||||||||||
| Status: | Peer Reviewed | |||||||||||||||||||||
| Publication Status: | Published | |||||||||||||||||||||
| Access rights to Published version: | Open Access | |||||||||||||||||||||
| RIOXX Funder/Project Grant: |
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