Intramolecular dipolar cycloaddition reactions of azomethine ylides

被引:983
作者
Coldham, I [1 ]
Hufton, R
机构
[1] Univ Sheffield, Dept Chem, Sheffield S3 7HF, S Yorkshire, England
[2] Tripos Discovery Res Ltd, Bude EX23 8LY, England
关键词
D O I
10.1021/cr040004c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Since the first intramolecular 1,3-dipolar cycloaddition reaction of an azomethine ylide was reported in 1976, various useful methods for the formation of azomethine ylides and the determination of the requirements for a successful intramolecular cycloaddition reaction have been developed. This review describes the background and mechanisms of azomethine ylide formation and intramolecular cycloaddition, giving a critical account including the very first example and covering the early 2005. The review is intended to be a useful resource for chemists interested in cycloaddition reactions and will inspire further exciting developments in this area.
引用
收藏
页码:2765 / 2809
页数:45
相关论文
共 204 条
[1]   ELECTROSTATIC EFFECTS IN 1,3-DIPOLAR CYCLOADDITION REACTIONS TO CHIRAL ALLYL ETHERS - A RATIONALE FOR THE EXPERIMENTALLY OBSERVED DIASTEREOSELECTIVITIES [J].
ANNUNZIATA, R ;
BENAGLIA, M ;
CINQUINI, M ;
RAIMONDI, L .
TETRAHEDRON, 1993, 49 (38) :8629-8636
[2]  
[Anonymous], 1984, 1,3-Dipolar Cycloaddition Chemistry
[3]  
[Anonymous], 1989, Adv. Heterocycl. Chem, DOI DOI 10.1016/S0065-2725(08)60332-3
[4]  
[Anonymous], 1991, Comprehensive Organic Synthesis
[5]  
[Anonymous], 1991, Comprehensive Organic Synthesis
[6]  
[Anonymous], 2003, Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry towards Heterocycles and Natural Products
[7]   X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .19. INTRAMOLECULAR CYCLO-ADDITIONS OF NON-STABILIZED AZOMETHINE YLIDES GENERATED VIA THE DECARBOXYLATIVE ROUTE FROM ALPHA-AMINO-ACIDS [J].
ARDILL, H ;
GRIGG, R ;
SRIDHARAN, V ;
SURENDRAKUMAR, S .
TETRAHEDRON, 1988, 44 (15) :4953-4966
[8]   X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .5. INTRAMOLECULAR CYCLO-ADDITIONS OF IMINES OF ALPHA-AMINO-ACID ESTERS [J].
ARMSTRONG, P ;
GRIGG, R ;
JORDAN, MW ;
MALONE, JF .
TETRAHEDRON, 1985, 41 (17) :3547-3558
[9]   A theoretical study on the regioselectivity of 1,3-dipolar cycloadditions using DFT-based reactivity indexes [J].
Aurell, MJ ;
Domingo, LR ;
Pérez, P ;
Contreras, R .
TETRAHEDRON, 2004, 60 (50) :11503-11509
[10]   Munchnone-alkene cycloadditions: Deviations from the FMO theory. Theoretical studies in the search of the transition state [J].
Avalos, M ;
Babiano, R ;
Cabanillas, A ;
Cintas, P ;
Jimenez, JL ;
Palacios, JC ;
Aguilar, MA ;
Corchado, JC ;
EspinosaGarcia, J .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (21) :7291-7297