N-Heterocyclic Carbene-Catalyzed [2+2+2] Annulation of Allenoates with Trifluoromethylketones

被引:36
作者
Sun Lihui [1 ]
Wang Tong [1 ]
Ye Song [1 ]
机构
[1] Chinese Acad Sci, Inst Chem, Beijing Natl Lab Mol Sci, CAS Key Lab Mol Recognit & Funct, Beijing 100190, Peoples R China
关键词
NHC-catalyzed; 2+2+2] annulations; allenoates; trifluoromethylketones; ELECTRON-DEFICIENT OLEFINS; BAYLIS-HILLMAN REACTION; ONE-POT SYNTHESIS; 3+2 CYCLOADDITION; ALLENIC ESTERS; NUCLEOPHILIC CARBENES; PHOSPHINE; ALDEHYDES; IMINES; KETONES;
D O I
10.1002/cjoc.201100383
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In contrast with the reported phosphine- and DABCO-catalyzed [3+2] and [2+2] annulation of allenoates with trifluoromethylketone, the [2+2+2] annulation of allenoates and two molecules of trifluoromethylketone was found under the condition of N-heterocyclic carbene catalysis.
引用
收藏
页码:190 / 194
页数:5
相关论文
共 78 条
[1]   A STABLE CRYSTALLINE CARBENE [J].
ARDUENGO, AJ ;
HARLOW, RL ;
KLINE, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (01) :361-363
[2]   Fused polycyclic nucleophilic carbenes - synthesis, structure, and function [J].
Arduengo, Anthony J., III ;
Iconaru, Luigi I. .
DALTON TRANSACTIONS, 2009, (35) :6903-6914
[3]   N-Heterocyclic Carbene Catalyzed [2+2] Cycloaddition of Aryl Isothiocyanates and Nitroolefins: An Efficient Synthesis of β-Thiolactams [J].
Awasthi, Chhama ;
Yadav, Lal Dhar S. .
SYNLETT, 2010, (12) :1783-1788
[4]  
Bogevig A, 2002, CHEM-EUR J, V8, P5652, DOI 10.1002/1521-3765(20021216)8:24<5652::AID-CHEM5652>3.0.CO
[5]  
2-J
[7]   Organocatalyzed conjugate umpolung of α,β-unsaturated aldehydes for the synthesis of γ-butyrolactones [J].
Burstein, C ;
Glorius, F .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (45) :6205-6208
[8]   Highly stereoselective formal [3+3] cycloaddition of enals and azomethine imines catalyzed by N-heterocyclic carbenes [J].
Chan, Audrey ;
Scheidt, Karl A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (17) :5334-+
[9]   Catalytic generation of activated carboxylates:: Direct, stereoselective synthesis of β-hydroxyesters from epoxyaldehydes [J].
Chow, KYK ;
Bode, JW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (26) :8126-8127
[10]  
Cowen B. J., 2009, CHEM SOC REV, V38, P3102, DOI DOI 10.1039/B816700C