芳基硼酸催化仲醇和叔醇的外消旋化反应
Arylboronic Acid-Catalyzed Racemization of Secondary and Tertiary Alcohols.
作者信息
Boyce Gregory R, Musolino Stefania F, Yang Jianing, Smith Andrew D, Taylor James E
机构信息
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.
出版信息
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。
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