N-tert-Butyl Triazolylidenes: Catalysts for the Enantioselective (3+2) Annulation of ,-Unsaturated Acyl Azoliums

被引：93
|
作者：
Candish, Lisa [1 ]
Forsyth, Craig M. [1 ]
Lupton, David W. [1 ]
机构：
[1] Monash Univ, Sch Chem, Clayton, Vic 3800, Australia
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 35期
基金：
澳大利亚研究理事会;
关键词：
cyclization; enantioselectivity; N-heterocyclic carbene; organocatalysis; synthetic methods; INTERMOLECULAR STETTER REACTIONS; HETEROCYCLIC CARBENE; BENZOIN CONDENSATION; 4+2 CYCLOADDITION; TRIAZOLIUM SALTS; NHC; REARRANGEMENT; DERIVATIVES; KETENES; HYDROACYLATION;
D O I：
10.1002/anie.201304081
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
But(yl) not futile: A range of N-tert-butyl-substituted triazolylidene N-heterocyclic carbenes have been prepared. Of these, the morpholinone-derived catalyst (1) proved best suited to the enantioselective synthesis of cyclopentanes from donor-acceptor cyclopropanes and α,β-unsaturated acyl fluorides. The performance of this catalyst has been correlated to the electronic nature of the catalyst by 13CNMR analysis. M.S.=molecular sieves, TMS=trimethylsilyl. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：9149 / 9152
页数：4
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