Boyce Gregory R, Musolino Stefania F, Yang Jianing, Smith Andrew D, Taylor James E
EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife KY16 9ST, U.K.
Department of Chemistry and Physics, Florida Gulf Coast University, Fort Myers, Florida 33965, United States.
J Org Chem. 2022 Oct 7;87(19):13367-13374. doi: 10.1021/acs.joc.2c01602. Epub 2022 Sep 8.
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.
已证明使用2-羧基苯硼酸（5摩尔%）和草酸（10摩尔%），以2-丁酮作为溶剂，可实现一系列对映体纯的仲醇和叔醇的外消旋化。据推测，该过程通过一个非手性碳正离子中间体，经由可逆的布朗斯特酸催化的C-O键断裂来进行。
