Catalytic MBH reaction of β-substituted nitroalkenes with azodicarboxylates

被引:29
作者
Chen, Xiang-Yu [1 ]
Xia, Fei [1 ]
Ye, Song [1 ]
机构
[1] Chinese Acad Sci, Inst Chem, Key Lab Mol Recognit & Funct, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China
基金
中国国家自然科学基金;
关键词
BAYLIS-HILLMAN REACTION; ASYMMETRIC MICHAEL ADDITION; TO-TAIL DIMERIZATION; CONJUGATED NITROALKENES; HIGHLY EFFICIENT; NUCLEOPHILIC CARBENES; ANTICANCER ACTIVITY; 4+2 CYCLOADDITION; MECHANISM; ALDEHYDES;
D O I
10.1039/c3ob40804c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An unprecedented N-heterocyclic carbene (NHC) catalyzed Morita-Baylis-Hillman (MBH) reaction of beta-substituted nitroalkenes and azodicarboxylates has been developed. Both beta-aryl and beta-alkyl nitroalkenes worked well for the reaction using 5 mol% of NHC catalyst, giving the desired alpha-hydrazino-alpha,beta-unsaturated nitroalkenes in good to excellent yields.
引用
收藏
页码:5722 / 5726
页数:5
相关论文
共 73 条
[1]  
[Anonymous], SYNTHESIS
[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 rearrangements of vinyl sulfones [J].
Atienza, Roxanne L. ;
Roth, Howard S. ;
Scheidt, Karl A. .
CHEMICAL SCIENCE, 2011, 2 (09) :1772-1776
[4]   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
[5]   Recent synthetic developments in the nitro to carbonyl conversion (Nef reaction) [J].
Ballini, R ;
Petrini, M .
TETRAHEDRON, 2004, 60 (05) :1017-1047
[6]   CONJUGATED NITROALKENES - VERSATILE INTERMEDIATES IN ORGANIC-SYNTHESIS [J].
BARRETT, AGM ;
GRABOSKI, GG .
CHEMICAL REVIEWS, 1986, 86 (05) :751-762
[7]   The Baylis-Hillman reaction: A novel carbon-carbon bond forming reaction [J].
Basavaiah, D ;
Rao, PD ;
Hyma, RS .
TETRAHEDRON, 1996, 52 (24) :8001-8062
[8]   Recent advances in the Baylis-Hillman reaction and applications [J].
Basavaiah, D ;
Rao, AJ ;
Satyanarayana, T .
CHEMICAL REVIEWS, 2003, 103 (03) :811-891
[9]   The Baylis-Hillman reaction: a novel concept for creativity in chemistry [J].
Basavaiah, Deevi ;
Veeraraghavaiah, Gorre .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (01) :68-78
[10]   Recent Contributions from the Baylis-Hillman Reaction to Organic Chemistry [J].
Basavaiah, Deevi ;
Reddy, Bhavanam Sekhara ;
Badsara, Satpal Singh .
CHEMICAL REVIEWS, 2010, 110 (09) :5447-5674