Kinetic Resolution of 1,1′-Biaryl-2,2′-Diols and Amino Alcohols through NHC-Catalyzed Atroposelective Acylation

被引：192

作者：

Lu, Shenci ^{[1
]}

Poh, Si Bei ^{[1
]}

Zhao, Yu ^{[1
]}

机构：

[1] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 41期

基金：

新加坡国家研究基金会;

关键词：

acylation; axial chirality; enantioselectivity; kinetic resolution; N-heterocyclic carbene; AXIALLY CHIRAL BIARYLS; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; SECONDARY ALCOHOLS; DERIVATIVES; LIGANDS; 2-NAPHTHOLS; CONVERSION; OXIDATION; MECHANISM;

D O I：

10.1002/anie.201406192

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We present here a highly efficient NHC-catalyzed kinetic resolution of a wide range of 1,1'-biaryl-2,2'-diols and amino alcohols to provide them in uniformly >99% ee. This represents the first highly enantioselective catalytic acylation of axially chiral alcohols. The aldehyde backbone that is incorporated into the chiral acyl azolium intermediate was found to have a significant effect on the enantioselectivity of the process.

引用

页码：11041 / 11045

页数：5

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