Spiro-oxindoles via bimetallic [Pd(0)/Ag(I)] catalytic intramolecular Heck-1,3-dipolar cycloaddition cascade reactions

被引：42

作者：

Grigg, R ^{[1
]}

Millington, EL ^{[1
]}

Thornton-Pett, M ^{[1
]}

机构：

[1] Univ Leeds, Sch Chem, MIDAS Ctr, Leeds LS2 9JT, W Yorkshire, England

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 14期

关键词：

D O I：

10.1016/S0040-4039(02)00331-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The combination of an intramolecular Heck reaction with a subsequent Ag(l) catalysed imine --> azomethine ylide --> cycloaddition cascade is described for the formation of novel spiro-oxindoles. The reaction proceeds regiospecifically with good to excellent stereoselectivity and creates two new rings, three bonds and three stereocentres. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：2605 / 2608

页数：4

共 28 条

[1] Palladium-catalysed carbomethoxyvinylation and thienylation of 5-iodo(bromo)-2,4-dimethoxypyrimidine in water
Basnak, I
Takatori, S
Walker, RT
[J]. TETRAHEDRON LETTERS, 1997, 38 (27) : 4869 - 4872
[2] TANDEM DIAZOTIZATION HECK REACTIONS - A GENERAL-SYNTHESIS OF SUBSTITUTED STYRENES FROM ANILINES
BELLER, M
FISCHER, H
KUHLEIN, K
[J]. TETRAHEDRON LETTERS, 1994, 35 (47) : 8773 - 8776
[3] SEQUENTIAL AND CASCADE [2+2]-CYCLOADDITION-PALLADIUM CATALYZED CYCLIZATION - BICYCLIC BETA-LACTAMS
BURWOOD, M
DAVIES, B
DIAZ, I
GRIGG, R
MOLINA, P
SRIDHARAN, V
HUGHES, M
[J]. TETRAHEDRON LETTERS, 1995, 36 (49) : 9053 - 9056
[4] Novel mammalian cell cycle inhibitors, cyclotryprostatins A-D, produced by Aspergillus fumigatus, which inhibit mammalian cell cycle at G2/M phase
Cui, CB
Kakeya, H
Osada, H
[J]. TETRAHEDRON, 1997, 53 (01) : 59 - 72
[5] Novel mammalian cell cycle inhibitors, tryprostatins A, B and other diketopiperazines produced by Aspergillus fumigatus .1. Taxonomy, fermentation, isolation and biological properties
Cui, CB
Kakeya, H
Okada, G
Onose, R
Osada, H
[J]. JOURNAL OF ANTIBIOTICS, 1996, 49 (06) : 527 - 533
[6] Sequential 1,3-dipolar cycloaddition-Pictet-Spengler reactions. A versatile tactical combination
Dondas, HA
Duraisingham, J
Grigg, R
MacLachlan, WS
MacPherson, DT
Thornton-Pett, M
Sridharan, V
Suganthan, S
[J]. TETRAHEDRON, 2000, 56 (24) : 4063 - 4070
[7] Total synthesis of spirotryprostatin A, leading to the discovery of some biologically promising analogues
Edmondson, S
Danishefsky, SJ
Sepp-Lorenzino, L
Rosen, N
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (10) : 2147 - 2155
[8] Sequential and cascade palladium catalysed cyclisation-anion capture-olefin metathesis
Evans, P
Grigg, R
Ramzan, MI
Sridharan, V
York, M
[J]. TETRAHEDRON LETTERS, 1999, 40 (15) : 3021 - 3024
[9] Cascade and sequential palladium catalysed cyclisation-azide capture-1,3-dipolar cycloaddition route to complex triazoles.
Gardiner, M
Grigg, R
Sridharan, V
Vicker, N
[J]. TETRAHEDRON LETTERS, 1998, 39 (5-6) : 435 - 438
[10] X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .21. ACTIVATION OF THE ZH PROTON IN IMINES
GRIGG, R
DONEGAN, G
GUNARATNE, HQN
KENNEDY, DA
MALONE, JF
SRIDHARAN, V
THIANPATANAGUL, S
[J]. TETRAHEDRON, 1989, 45 (06) : 1723 - 1746

← 1 2 3 →