Access to Enantiopure Triarylmethanes and 1,1-Diarylalkanes by NHC-Catalyzed Acylative Desymmetrization

被引：36

作者：

Lu, Shenci ^{[1
]}

Song, Xiaoxiao ^{[1
]}

Poh, Si Bei ^{[1
]}

Yang, Hui ^{[1
]}

Wong, Ming Wah ^{[1
]}

Zhao, Yu ^{[1
]}

机构：

[1] Natl Univ Singapore, Dept Chem, 3 Sci Dr 3, Singapore 117543, Singapore

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2017年 / 23卷 / 10期

基金：

新加坡国家研究基金会;

关键词：

1,1-diarylalkanes; acylation; carbenes; desymmetrization; N-heterocycles; CROSS-COUPLING REACTIONS; DYNAMIC KINETIC RESOLUTION; N-HETEROCYCLIC CARBENES; BARRIER HYDROGEN-BONDS; ASYMMETRIC-SYNTHESIS; ESTERS; ALCOHOLS; DIARYLMETHYLAMINES; CONSTRUCTION; SELECTIVITY;

D O I：

10.1002/chem.201605445

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We present herein an unprecedented, efficient and enantioselective synthesis of triarylmethanes and 1,1-diarylalkanes through N-heterocyclic carbene-catalyzed acylative desymmetrization of bisphenols. This method utilizes readily available substrates, reagents and a simple procedure to deliver the valuable products in excellent enantiopurity. DFT calculations reveal that the selectivity is governed by the C-C bond cleavage step of the tetrahedral intermediate leading to the ester product. A transition state model featuring a combination of intramolecular hydrogen bond and steric effect is developed to explain the enantioselectivity.

引用

页码：2275 / 2281

页数：7

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