Arylboronic Acid-Catalyzed Racemization of Secondary and Tertiary Alcohols

Gregory Boyce, Stefania Musolino, Jianing Yang, Andrew Smith, James Taylor

Research output: Contribution to journalArticlepeer-review

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
JournalJournal of Organic Chemistry
Volume87
Issue number19
DOIs
Publication statusPublished - 7 Oct 2022

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