Enantioselective N-Heterocyclic Carbene Catalysis via the Dienyl Acyl Azolium

被引：45

作者：

Gillard, Rachel M. ^{[1
]}

Fernando, Jared E. M. ^{[1
]}

Lupton, David W. ^{[1
]}

机构：

[1] Monash Univ, Sch Chem, Clayton, Vic 3800, Australia

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 17期

基金：

澳大利亚研究理事会;

关键词：

1,6-addition; dienyl acyl azolium; enantioselective catalysis; N-heterocyclic carbene; beta-lactonization; INTRAMOLECULAR STETTER REACTION; SUBSTITUTED BETA-LACTONES; CARBON 4+2 ANNULATION; ASYMMETRIC-SYNTHESIS; LEWIS-ACID; CYCLOADDITION REACTION; DISUBSTITUTED KETENES; DOMINO REACTIONS; DELTA-LACTONES; NHC CATALYSIS;

D O I：

10.1002/anie.201712604

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein we report the enantioselective N-heterocyclic carbene catalyzed (4+2) annulation of the dienyl acyl azolium with enolates. The reaction exploits readily accessible acyl fluorides and TMS enol ethers to give a range of highly enantio- and diastereo-enriched cyclohexenes (most > 97:3 er and > 20:1 dr). The reaction was found to require high nucleophilicity NHC catalysts with mechanistic studies supporting a stepwise 1,6-addition/beta-lactonization.

引用

页码：4712 / 4716

页数：5

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