Unprecedented 1,3-dipolar cycloaddition of azomethine ylides to ester carbonyl

被引：25

作者：

Novikov, MS

Voznyi, IV

Khlebnikov, AF

Kopf, J

Kostikov, RR

机构：

[1] St Petersburg State Univ, Dept Chem, St Petersburg 198504, Russia

[2] Univ Hamburg, Inst Inorgan Chem, D-20146 Hamburg, Germany

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2002年 / 14期

关键词：

D O I：

10.1039/b204464a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Fluorinated azomethine ylides generated by the reaction of difluorocarbene with aryl and alkyl imines of O-acylated salicylaldehyde undergo intramolecular 1,3-dipolar cyclo-addition across the ester carbonyl to give 2,8-dioxa-6- azabicyclo[3.2.1]octane derivatives.

引用

收藏

页码：1628 / 1630

页数：3

相关论文

共 27 条

[1]

[Anonymous], 1989, Adv. Heterocycl. Chem, DOI DOI 10.1016/S0065-2725(08)60332-3

[2]

[Anonymous], 1984, 13 DIPOLAR CYCLOADDI

[3]

BENDE Z, 1982, LIEBIGS ANN CHEM, P2146

[4]

BENDE Z, 1982, LIEBIGS ANN CHEM, P924

[5] Microwave-induced 1,3-dipolar intramolecular cycloadditions of N-substituted oximes, nitrones, and azomethine ylides for the chiral synthesis of functionalized nitrogen heterocycles [J].

Cheng, Q ;

Zhang, W ;

Tagami, Y ;

Oritani, T .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (04) :452-456

[6] Intramolecular azomethine ylide cycloaddition reactions to give octahydroindoles [J].

Coldham, I ;

Crapnell, KM ;

Moseley, JD ;

Rabot, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (15) :1758-1763

[7] INTERMOLECULAR AND INTRAMOLECULAR AZOMETHINE YLIDE [3 + 2] DIPOLAR CYCLO-ADDITIONS FOR THE SYNTHESIS OF HIGHLY FUNCTIONALIZED PYRROLES AND PYRROLIDINES [J].

DESHONG, P ;

KELL, DA ;

SIDLER, DR .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (13) :2309-2315

[8] A stereoselective synthesis of 3-substituted hexahydroindeno[2,1-b]pyrroles via an intramolecular azomethine ylide cycloaddition [J].

Harling, JD ;

Orlek, BS .

TETRAHEDRON, 1998, 54 (49) :14905-14912

[9] TANDEM GENERATION AND INTRAMOLECULAR TRAPPING OF CHIRAL STABILIZED AZOMETHINE YLIDES WITH ALKYNE DIPOLAROPHILES [J].

HARWOOD, LM ;

KITCHEN, LC .

TETRAHEDRON LETTERS, 1993, 34 (41) :6603-6606

[10] INTRAMOLECULAR 1,3-DIPOLAR CYCLOADDITION OF STABILIZED AZOMETHINE YLIDES TO UNACTIVATED DIPOLAROPHILES [J].

HENKE, BR ;

KOUKLIS, AJ ;

HEATHCOCK, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (26) :7056-7066