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
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2013年 / 11卷 / 34期
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
[51]   Organocatalyzed Michael Addition of Aldehydes to Nitro Alkenes - Generally Accepted Mechanism Revisited and Revised [J].
Patora-Komisarska, Krystyna ;
Benohoud, Meryem ;
Ishikawa, Hayato ;
Seebach, Dieter ;
Hayashi, Yujiro .
HELVETICA CHIMICA ACTA, 2011, 94 (05) :719-745
[52]   α-Hydroxymethylation of conjugated nitroalkenes via the Morita-Baylls-Hillman reaction [J].
Rastogi, N ;
Namboothiri, INN ;
Cojocaru, M .
TETRAHEDRON LETTERS, 2004, 45 (24) :4745-4748
[53]   Synthesis and anticancer activity studies of α-aminoalkylated conjugated nitroalkenes [J].
Rastogi, Namrata ;
Mohan, Renu ;
Panda, Dulal ;
Mobin, Shaikh M. ;
Namboothiri, Irishi N. N. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (17) :3211-3214
[54]   Development of chiral bicyclic triazolium salt organic catalysts:: The importance of the N-aryl substituent [J].
Rovis, Tomislav .
CHEMISTRY LETTERS, 2008, 37 (01) :2-7
[55]   Rauhut-Currier type homo- and heterocouplings involving nitroalkenes and nitrodienes [J].
Shanbhag, Pramod ;
Nareddy, Pradeep R. ;
Dadwal, Mamta ;
Mobin, Shaikh M. ;
Namboothiri, Irishi N. N. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (21) :4867-4873
[56]   Probing the Mechanism of Baylis-Hillman Reaction in Ionic Liquids [J].
Singh, Anshu ;
Kumar, Anil .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (19) :8775-8779
[57]   Advances in the Baylis-Hillman reaction-assisted synthesis of cyclic frameworks [J].
Singh, Vijay ;
Batra, Sanjay .
TETRAHEDRON, 2008, 64 (20) :4511-4574
[58]   N-heterocyclic carbene catalyzed C-C bond cleavage in redox esterifications of chiral formylcyclopropanes [J].
Sohn, Stephanie S. ;
Bode, Jeffrey W. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (36) :6021-6024
[59]   N-Heterocyclic Carbene-Catalyzed [2+2+2] Annulation of Allenoates with Trifluoromethylketones [J].
Sun Lihui ;
Wang Tong ;
Ye Song .
CHINESE JOURNAL OF CHEMISTRY, 2012, 30 (01) :190-194
[60]   Intermolecular cross-double-Michael addition between nitro and carbonyl activated olefins as a new approach in C-C bond formation [J].
Sun, Xiaohua ;
Sengupta, Sujata ;
Petersen, Jeffrey L. ;
Wang, Hong ;
Lewis, James P. ;
Shi, Xiaodong .
ORGANIC LETTERS, 2007, 9 (22) :4495-4498
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