First thermal and transition metal catalysed intramolecular [4+2] cycloaddition reactions with N-tethered ynamides

被引:72
作者
Witulski, B [1 ]
Lumtscher, J [1 ]
Bergsträsser, U [1 ]
机构
[1] Univ Kaiserslautern, Fachbereich Chem, D-67663 Kaiserslautern, Germany
关键词
ynamides; tetrahydroindoles; Diels-Alder reaction; catalysis; alkynyliodonium salts;
D O I
10.1055/s-2003-38357
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cationic rhodium(1)-complexes generated fro m [RhCl(PPh3)(3)] and AgSbF6 catalyse at room temperature the first examples of intramolecular [4+2] cycloaddition reactions with N- tethered ynamides and provide an efficient access to synthetically versatile tetrahydroindoles.
引用
收藏
页码:708 / 710
页数:3
相关论文
共 50 条
[1]   A NEW DOMINO SYNTHESIS OF POLYFUNCTIONALIZED PENTASUBSTITUTED PYRIDINES [J].
BARLUENGA, J ;
FERRERO, M ;
PELAEZARANGO, E ;
LOPEZORTIZ, F ;
PALACIOS, F .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (07) :865-866
[2]   INVERSE ELECTRON DEMAND DIELS-ALDER REACTIONS OF 2,4,6-TRIS(ETHOXYCARBONYL)-1,3,5-TRIAZINE AND 2,4,6-TRIS(METHYLTHIO)-1,3,5-TRIAZINE - PYRIMIDINE INTRODUCTION [J].
BOGER, DL ;
DANG, Q .
TETRAHEDRON, 1988, 44 (11) :3379-3390
[3]   Total synthesis of Amaryllidaceae alkaloids utilizing sequential intramolecular heterocyclic azadiene Diels-Alder reactions of an unsymmetrical 1,2,4,5-tetrazine [J].
Boger, DL ;
Wolkenberg, SE .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (26) :9120-9124
[4]  
Corey EJ, 2002, ANGEW CHEM INT EDIT, V41, P1650, DOI 10.1002/1521-3773(20020517)41:10<1650::AID-ANIE1650>3.0.CO
[5]  
2-B
[6]   Phosphabenzenes as electron withdrawing phosphine ligands in catalysis [J].
DiMauro, EF ;
Kozlowski, MC .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (03) :439-444
[7]   Intramolecular Diels-Alder reactions of N-substituted oxazolones [J].
Fearnley, SP ;
Market, E .
CHEMICAL COMMUNICATIONS, 2002, (05) :438-439
[8]   Stereoselective, intermolecular dienyltosylamide/alkynyliodonium salt additions in the synthesis of fused bicyclic dihydropyrrole derivatives [J].
Feldman, KS ;
Mareska, DA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (16) :4027-4028
[9]  
Fringuelli F., 2002, The Diels-Alder Reaction: Selected Practical Methods
[10]  
GENET JP, 1979, TETRAHEDRON LETT, P1499