Nanocrystalline copper(II) oxide catalyzed aza-Michael reaction and insertion of α-diazo compounds into N-H bonds of amines

被引:49
作者
Kantam, M. Lakshmi [1 ]
Laha, Soumi [1 ]
Yadav, Jagjit [1 ]
Jha, Shailendra [2 ]
机构
[1] Indian Inst Chem Technol, Inorgan & Phys Chem Div, Hyderabad 500007, Andhra Pradesh, India
[2] Jadavpur Univ, Dept Chem, Kolkata, India
关键词
Nanocrystalline copper(II) oxide; Heterogeneous catalyst; Aza-Michael addition; alpha; beta-Unsaturated compounds; Insertion; Diazoacetate; EFFICIENT HETEROGENEOUS CATALYST; SOLVENT-FREE CONDITIONS; ONE-STEP SYNTHESIS; ALPHA; BETA-ETHYLENIC COMPOUNDS; RHODIUM CARBENOIDS; ENANTIOSELECTIVE SYNTHESIS; CONJUGATE ADDITION; ACID-DERIVATIVES; ALIPHATIC-AMINES; MGO;
D O I
10.1016/j.tetlet.2009.05.059
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Nanocrystalline copper(II) oxide efficiently catalyzed the conjugate addition of aliphatic amines to alpha,beta-unsaturated compounds to produce beta-amino compounds with excellent yields under mild reaction conditions. Similarly, Glycine esters are obtained in good yields by the insertion of alpha-diazoacetate into N-H bonds of amines. The catalyst is used for three cycles with minimal loss of activity. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4467 / 4469
页数:3
相关论文
共 56 条
[1]   N-H insertion reactions of rhodium carbenoids .1. Preparation of alpha-amino acid and alpha-aminophosphonic acid derivatives [J].
Aller, E ;
Buck, RT ;
Drysdale, MJ ;
Ferris, L ;
Haigh, D ;
Moody, CJ ;
Pearson, ND ;
Sanghera, JB .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (24) :2879-2884
[2]   BETA-LACTAMS FROM ESTER ENOLATES AND SILYLIMINES - ENANTIOSELECTIVE SYNTHESIS OF THE TRANS-CARBAPENEM ANTIBIOTICS (+)-PS-5 AND (+)-PS-6 [J].
ANDREOLI, P ;
CAINELLI, G ;
PANUNZIO, M ;
BANDINI, E ;
MARTELLI, G ;
SPUNTA, G .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (21) :5984-5990
[3]   LiClO4 accelerated Michael addition of amines to α,β-unsaturated olefins under solvent-free conditions [J].
Azizi, N ;
Saidi, MR .
TETRAHEDRON, 2004, 60 (02) :383-387
[4]   Cu(I)-carbenoid- and Ag(I)-Lewis acid-catalyzed asymmetric intermolecular insertion of α-diazo compounds into N-H bonds [J].
Bachmann, S ;
Fielenbach, D ;
Jorgensen, KA .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (20) :3044-3049
[5]   Improved heteroatom nucleophilic addition to electron-poor alkenes promoted by CeCl3•7H2O/NaI system supported on alumina in solvent-free conditions [J].
Bartoli, G ;
Bartolacci, M ;
Giuliani, A ;
Marcantoni, E ;
Massaccesi, M ;
Torregiani, E .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (01) :169-174
[6]   CHEMOSELECTIVE AND DIASTEREOSELECTIVE REDUCTION OF BETA-ENAMINO ESTERS - A CONVENIENT SYNTHESIS OF BOTH CIS-GAMMA-AMINO AND TRANS-GAMMA-AMINO ALCOHOLS AND BETA-AMINO ESTERS [J].
BARTOLI, G ;
CIMARELLI, C ;
MARCANTONI, E ;
PALMIERI, G ;
PETRINI, M .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (18) :5328-5335
[7]   N-H Insertion reactions of rhodium carbenoids. Part 3. The development of a modified Bischler indole synthesis and a new protecting-group strategy for indoles [J].
Bashford, KE ;
Cooper, AL ;
Kane, PD ;
Moody, CJ ;
Muthusamy, S ;
Swann, E .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (14) :1672-1687
[8]   Synthesis of β-amino esters via aza-Michael addition of amines to alkenes promoted on silica:: A useful and recyclable surface [J].
Basu, B ;
Das, P ;
Hossain, I .
SYNLETT, 2004, (14) :2630-2632
[9]   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
[10]   One-step synthesis of methyl isobutyl ketone from acetone and hydrogen over Cu-on-MgO catalysts [J].
Chikán, V ;
Molnár, A ;
Balázsik, K .
JOURNAL OF CATALYSIS, 1999, 184 (01) :134-143