Horeau amplification in the sequential acylative kinetic resolution of (±)-1,2-diols and (±)-1,3-diols in flow
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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 involve eight independent rate constants.
Brandolese , A , Greenhalgh , M D , Desrues , T , Liu , X , Qu , S , Bressy , C & Smith , A D 2021 , ' Horeau amplification in the sequential acylative kinetic resolution of (±)-1,2-diols and (±)-1,3-diols in flow ' , Organic & Biomolecular Chemistry , vol. 19 , no. 16 , pp. 3620-3627 . https://doi.org/10.1039/D1OB00304F
Organic & Biomolecular Chemistry
Copyright © 2021 The Author(s). Open Access. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
DescriptionWe gratefully acknowledge the University of Ferrara (Bando Giovani Ricercatori 2019) for financial support (AB). The Chinese Scholarship Scheme and University of St Andrews are thanked for a CSC Scholarship (S. Q.). Aix-Marseille University, CNRS, and ANR (Agence Nationale de la Recherche) (AMPLI project ANR-18-CE07-0036) are also gratefully acknowledged for funding (TD, XL and CB).
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