Ene-yne-ene and ene-yne-yne metathesis of norbornene derivatives

被引:16
作者
Banti, D [1 ]
North, M [1 ]
机构
[1] Kings Coll London, Dept Chem, London WC2R 2LS, England
关键词
D O I
10.1016/j.tetlet.2003.09.035
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Norbornene derivatives 4 and 5 containing sidechains bearing an internal alkyne and either a terminal alkene or a terminal alkyne were found to undergo a cascade of metathesis reactions when treated with ruthenium based metathesis catalysts to form highly functionalised pentacyclic products. The reactions illustrate an interesting difference in reactivity between Grubbs' catalyst and the second generation catalyst, with the former being more reactive for the early steps of the cascade. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8157 / 8160
页数:4
相关论文
共 35 条
[1]  
Banti D, 2002, ADV SYNTH CATAL, V344, P694, DOI 10.1002/1615-4169(200208)344:6/7<694::AID-ADSC694>3.0.CO
[2]  
2-X
[3]   Totally atom economical tandem-metathesis and Diels-Alder approach to polycyclic compounds [J].
Banti, D ;
North, M .
TETRAHEDRON LETTERS, 2002, 43 (08) :1561-1564
[4]   Rapid entry into mono-, bi-, and tricyclic β-lactam arrays via alkene metathesis [J].
Barrett, AGM ;
Baugh, SPD ;
Braddock, DC ;
Flack, K ;
Gibson, VC ;
Giles, MR ;
Marshall, EL ;
Procopiou, PA ;
White, AJP ;
Williams, DJ .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22) :7893-7907
[5]  
Bielawski CW, 2000, ANGEW CHEM INT EDIT, V39, P2903, DOI 10.1002/1521-3773(20000818)39:16<2903::AID-ANIE2903>3.0.CO
[6]  
2-Q
[7]   Synthesis of trisubstituted alkenes via olefin cross-metathesis [J].
Chatterjee, AK ;
Grubbs, RH .
ORGANIC LETTERS, 1999, 1 (11) :1751-1753
[8]   Controlled living ring-opening-metathesis polymerization by a fast-initiating ruthenium catalyst [J].
Choi, TL ;
Grubbs, RH .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (15) :1743-1746
[9]   Tandem ring-closing metathesis reaction with a ruthenium catalyst containing a N-heterocyclic ligand [J].
Choi, TL ;
Grubbs, RH .
CHEMICAL COMMUNICATIONS, 2001, (24) :2648-2649
[10]  
Clercq B., 2002, ADV SYNTH CATAL, V344, P639