Arylboronic acid-catalyzed racemization of secondary and tertiary alcohols

Gregory Boyce, Stefania F. Musolino, Jianing Yang, Andrew D. Smith*, James Taylor

*Corresponding author for this work

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Abstract

The use of 2-carboxyphenylboronic acid (5 mol %) and oxalic acid (10 mol %) with 2-butanone as a solvent for the racemization of a range of enantiomerically pure secondary and tertiary alcohols is demonstrated. The process is postulated to proceed via reversible Brønsted acid-catalyzed C–O bond cleavage through an achiral carbocation intermediate.
Original languageEnglish
Pages (from-to)13367-13374
Number of pages8
JournalThe Journal of Organic Chemistry
Volume87
Issue number19
Early online date8 Sept 2022
DOIs
Publication statusPublished - 7 Oct 2022

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