Rapid Synthesis of 1,3,4,4-Tetrasubstituted β-Lactams from Methyleneaziridines Using a Four-Component Reaction

被引:140
作者
Cariou, Claire C. A. [1 ]
Clarkson, Guy J. [1 ]
Shipman, Michael [1 ]
机构
[1] Univ Warwick, Dept Chem, Coventry CV4 7AL, W Midlands, England
基金
英国工程与自然科学研究理事会;
关键词
D O I
10.1021/jo801664g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Graphics 2-Methyleneaziridines can be transformed into a variety of 1,3,4,4-tetrasubstituted beta-lactams in moderate to good yields (46-63%) via a "one-pot" process that brings together four components with the formation of three new intermolecular carbon-carbon bonds.
引用
收藏
页码:9762 / 9764
页数:3
相关论文
共 50 条
[1]   β-lactams:: Versatile building blocks for the stereoselective synthesis of non-β-lactam products [J].
Alcaide, Benito ;
Almendros, Pedro ;
Aragoncillo, Cristina .
CHEMICAL REVIEWS, 2007, 107 (11) :4437-4492
[2]   Spiro-aziridine and bislactam formation from bisketene-imine cycloadditions [J].
Allen, Annette D. ;
Godoy, Jazmin ;
Fu, Nanyan ;
Nagy, Michelle ;
Spaclaro, Sandra ;
Tidwell, Thomas T. ;
Vukovic, Sinisa .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (08) :2386-2387
[3]   α-oxohydrazones as imine component in the synthesis of 4-functionalized azetidinones by the Staudinger reaction [J].
Bianchi, L ;
Dell'Erba, C ;
Maccagno, M ;
Mugnoli, A ;
Novi, M ;
Petrillo, G ;
Sancassan, F ;
Tavani, C .
TETRAHEDRON, 2003, 59 (51) :10195-10201
[4]   Multi-component syntheses of heterocycles by transition-metal catalysis [J].
D'Souza, Daniel M. ;
Mueller, Thomas J. J. .
CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) :1095-1108
[5]   Stereoselective formation of quaternary carbon centers and related functions [J].
Denissova, I ;
Barriault, L .
TETRAHEDRON, 2003, 59 (51) :10105-10146
[6]   Direct, palladium-catalyzed, multicomponent synthesis of β-lactams from imines, acid chloride, and carbon monoxide [J].
Dhawan, Rajiv ;
Dghaym, Rania D. ;
St. Cyr, Daniel J. ;
Arndtsen, Bruce A. .
ORGANIC LETTERS, 2006, 8 (18) :3927-3930
[7]   Recent developments in isocyanide based multicomponent reactions in applied chemistry [J].
Dömling, A .
CHEMICAL REVIEWS, 2006, 106 (01) :17-89
[8]  
Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO
[9]  
2-U
[10]   Catalytic asymmetric synthesis of all-carbon quaternary stereocenters [J].
Douglas, CJ ;
Overman, LE .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) :5363-5367