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.
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页码：4712 / 4716
页数：5
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