Bismuth nitrate-catalyzed versatile Michael reactions

被引:462
作者
Srivastava, N [1 ]
Banik, BK [1 ]
机构
[1] Univ Texas, MD Anderson Canc Ctr, Dept Mol Pathol, Houston, TX 77030 USA
关键词
D O I
10.1021/jo026550s
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Bismuth nitrate-catalyzed versatile Michael reaction was developed to reduce the complications that characterize the current standard Michael reaction and used for facile preparation of organic compounds of widely different structures. For example, several substituted amines, imidazoles, thio compounds, indoles, and carbamates were prepared at room temperature by following this method. In contrast with the existing methods using many acidic catalysts, this method is very general, simple, high-yielding, environmentally friendly, and oxygen and moisture tolerant. However, the promoting role of bismuth nitrate in this reaction is not understood at this time.
引用
收藏
页码:2109 / 2114
页数:6
相关论文
共 62 条
[21]  
Bull SD, 2000, SYNLETT, P1257
[22]   CATALYSIS OF THE SPECIFIC MICHAEL ADDITION - THE EXAMPLE OF ACRYLATE ACCEPTORS [J].
CABRAL, J ;
LASZLO, P ;
MAHE, L ;
MONTAUFIER, MT ;
RANDRIAMAHEFA, SL .
TETRAHEDRON LETTERS, 1989, 30 (30) :3969-3972
[23]   A simple and efficient chemoselective method for the catalytic deprotection of acetals and ketals using bismuth triflate [J].
Carrigan, MD ;
Sarapa, D ;
Smith, RC ;
Wieland, LC ;
Mohan, RS .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (03) :1027-1030
[24]  
Christoffers J, 1998, EUR J ORG CHEM, V1998, P1259
[25]   Nickel(II)-catalyzed Michael additions.: Formation of quaternary centers and diastereoselective addition of enantiopure N-acetoacetyl-4-benzyloxazolidin-2-one [J].
Clariana, J ;
Gálvez, N ;
Marchi, C ;
Mañas, MM ;
Vallribera, A ;
Molins, E .
TETRAHEDRON, 1999, 55 (23) :7331-7344
[26]   A new entry to N-unsubstituted β-lactams through a solid-phase approach [J].
Dasgupta, SK ;
Banik, BK .
TETRAHEDRON LETTERS, 2002, 43 (51) :9445-9447
[27]  
DAVIES SG, 1995, SYNLETT, P700
[28]   Stereoselective synthesis of 2-aryloxy esters: An asymmetric approach to fluoxetine, tomoxetine and nisoxetine [J].
Devine, PN ;
Heid, RM ;
Tschaen, DM .
TETRAHEDRON, 1997, 53 (20) :6739-6746
[29]   A simple chemoselective method for the deprotection of acetals and ketals using bismuth nitrate pentahydrate [J].
Eash, KJ ;
Pulia, MS ;
Wieland, LC ;
Mohan, RS .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (24) :8399-8401
[30]   HIGHLY STEREOSELECTIVE SYNTHESES INVOLVING N-ALKYL-4,4,7-ALPHA-TRIMETHYL-TRANS-OCTAHYDRO-1,3-BENZOXAZINE INTERMEDIATES .2. [J].
ELIEL, EL ;
HE, XC .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (07) :2114-2119