Isothiourea-Catalysed Acylative Kinetic Resolution of Aryl-Alkenyl (sp2 vs. sp2) Substituted Secondary Alcohols

被引：24

作者：

Musolino, Stefania F. ^{[1
]}

Ojo, O. Stephen ^{[1
]}

Westwood, Nicholas J. ^{[1
]}

Taylor, James E. ^{[1
]}

Smith, Andrew D. ^{[1
]}

机构：

[1] Univ St Andrews, Sch Chem, EaStCHEM, St Andrews KY16 9ST, Fife, Scotland

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2016年 / 22卷 / 52期

基金：

英国工程与自然科学研究理事会;

关键词：

acylation; isothiourea; kinetic resolution; organocatalysis; renewable resources; ENANTIOSELECTIVE ACYL TRANSFER; ACHIRAL CARBOXYLIC-ACIDS; ALLYLIC ALCOHOLS; ASYMMETRIC ESTERIFICATION; PIVALIC ANHYDRIDE; SULFUR; HOMOBENZOTETRAMISOLE; BENZOTETRAMISOLE;

D O I：

10.1002/chem.201604788

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The non-enzymatic acylative kinetic resolution of challenging aryl-alkenyl (sp(2) vs. sp(2)) substituted secondary alcohols is described, with effective enantiodiscrimination achieved using the isothiourea organocatalyst HyperBTM (1 mol%) and isobutyric anhydride. The kinetic resolution of a wide range of aryl-alkenyl substituted alcohols has been evaluated, with either electron-rich or naphthyl aryl substituents in combination with an unsubstituted vinyl substituent providing the highest selectivity (S = 2-1980). The use of this protocol for the gram-scale (2.5 g) kinetic resolution of a model aryl-vinyl (sp(2) vs. sp(2)) substituted secondary alcohol is demonstrated, giving access to > 1 g of each of the product enantiomers both in 99:1 e.r.

引用

页码：18916 / 18922

页数：7

共 23 条

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