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

被引：187
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
收藏
页码：11041 / 11045
页数：5
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