Chloramphenicol base chemistry. Part 11:1 chloramphenicol base-derived thiourea-catalyzed enantioselective Michael addition of malononitrile to α,β-unsaturated ketones

被引：13

作者：

Yan, Linjie

Wang, Haifeng

Xiong, Fangjun

Tao, Yuan

Wu, Yan

Chen, Fener ^{[1
]}

机构：

[1] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China

来源：

TETRAHEDRON-ASYMMETRY | 2017年 / 28卷 / 07期

关键词：

HYDROGENATION/DYNAMIC KINETIC RESOLUTION; ASYMMETRIC CONJUGATE ADDITIONS; MESO-CYCLIC ANHYDRIDES; CHIRAL LEWIS-ACID; BIFUNCTIONAL ORGANOCATALYST; DUAL ACTIVATION; AMINE CATALYSTS; DERIVATIVES; IMIDES; ALCOHOLYSIS;

D O I：

10.1016/j.tetasy.2017.05.015

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The first chloramphenicol base-derived thiourea-catalyzed enantioselective Michael addition of malononitrile to alpha,beta-unsaturated ketones is reported. The Michael adducts were obtained in good to excellent yields (up to 98% yield) and enantioselectivities (up to 94% ee). This reaction has a broad substrate scope to various alpha,beta-unsaturated ketones. With this in mind, this methodology was successfully applied to the synthesis of a chiral piperidone, an advanced building block for dihydropyridinone P2X(7) receptor antagonists. (C) 2017 Published by Elsevier Ltd.

引用

页码：921 / 929

页数：9