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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 ISSN 1477-0520.

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Official URL: https://doi.org/10.1039/d1ob00304f

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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
Subjects: Q Science > QD Chemistry
T Technology > TR Photography
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:
DateEvent
2021Published
8 March 2021Available
8 March 2021Accepted
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 (Creative Commons)
Date of first compliant deposit: 30 November 2021
Date of first compliant Open Access: 3 December 2021
RIOXX Funder/Project Grant:
Project/Grant IDRIOXX Funder NameFunder ID
UNSPECIFIEDUniversità di Ferrara ‎ http://viaf.org/viaf/148474709
CSC Scholarship China. Yu yan wen zi xin xi guan li sihttp://viaf.org/viaf/296375668
CSC Scholarship University of St Andrewshttp://dx.doi.org/10.13039/501100000740
UNSPECIFIEDAix-Marseille Universitéhttp://dx.doi.org/10.13039/100007586
UNSPECIFIED[CNRS] Centre National de la Recherche Scientifiquehttp://dx.doi.org/10.13039/501100004794
UNSPECIFIED[ANR] Agence Nationale de la Recherchehttp://dx.doi.org/10.13039/501100001665
Is Part Of: 1

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