Transition-Metal-Free Decarboxylative Propargylic Substitution/Cyclization with either Azolium Enolates or Acyl Anions

被引：57
|
作者：
Lu, Shenci [1 ]
Ong, Jun-Yang [1 ,2 ]
Poh, Si Bei [1 ]
Tsang, Terence [1 ]
Zhao, Yu [1 ,2 ]
机构：
[1] NUS, Dept Chem, 3 Sci Dr 3, Singapore 117543, Singapore
[2] NUS, Grad Sch Integrat Sci Engn NGS, 28 Med Dr 3, Singapore 117456, Singapore
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 20期
关键词：
cycloaddition; decarboxylation; enantioselectivity; heterocycles; N-heterocyclic carbenes; N-HETEROCYCLIC CARBENES; DIELS-ALDER REACTIONS; ENANTIOSELECTIVE SYNTHESIS; CATALYZED HYDROACYLATION; COOPERATIVE CATALYSIS; ASYMMETRIC-SYNTHESIS; CASCADE REACTION; STETTER REACTION; BOND FORMATION; ANNULATION;
D O I：
10.1002/anie.201801340
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Presented herein is an unprecedented transition-metal-free propargylic substitution reaction with either azolium enolates or acyl anions, which are generated from aldehydes under N-heterocyclic carbene catalysis. This new catalytic activation operates on readily available cyclic propargylic carbamates through decarboxylation, and generates reactive allene intermediates that can undergo divergent cyclization pathways to deliver skeletally diverse polycyclic compounds with high levels of efficiency and excellent enantioselectivities.
引用
收藏
页码：5714 / 5719
页数：6
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