Horeau amplification in the sequential acylative kinetic resolution of (±)-1,2-diols and (±)-1,3-diols in flow

Arianna Brandolese, Mark David Greenhalgh, Titouan Desrues, Xueyang Liu, Shen Qu, Cyril Bressy, Andrew David Smith

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1 Citation (Scopus)

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 involve eight independent rate constants.
Original languageEnglish
Pages (from-to)3620-3627
Number of pages8
JournalOrganic & Biomolecular Chemistry
Volume19
Issue number16
Early online date8 Mar 2021
DOIs
Publication statusPublished - 28 Apr 2021

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