Arylboronic Acid-Catalyzed Racemization of Secondary and Tertiary Alcohols

被引：3
|
作者：
Boyce, Gregory R. [1 ,2 ]
Musolino, Stefania F. [1 ]
Yang, Jianing [1 ]
Smith, Andrew D. [1 ]
Taylor, James E. [3 ]
机构：
[1] Univ St Andrews, Sch Chem, EaStCHEM, St Andrews KY16 9ST, Fife, Scotland
[2] Florida Gulf Coast Univ, Dept Chem & Phys, Ft Myers, FL 33965 USA
[3] Univ Bath, Dept Chem, Bath, Avon BA2 7AY, England
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 19期
基金：
英国工程与自然科学研究理事会;
关键词：
DYNAMIC KINETIC RESOLUTION; AROMATIC ALCOHOLS; LOW-COST; EFFICIENT; ACTIVATION; MECHANISM; MILD;
D O I：
10.1021/acs.joc.2c01602
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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 Br??nsted acid-catalyzed C???O bond cleavage through an achiral carbocation intermediate. <comment>Superscript/Subscript Available</comment
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页码：13367 / 13374
页数：8
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