Ene-yne metathesis of polyunsaturated norbornene derivatives

被引：14

作者：

Banti, D ^{[1
]}

Groaz, E ^{[1
]}

North, M ^{[1
]}

机构：

[1] Kings Coll London, Dept Chem, London WC2R 2LS, England

来源：

TETRAHEDRON | 2004年 / 60卷 / 37期

关键词：

norbornene; metathesis; alkene; alkyne; Grubb's-catalyst; ruthenium;

D O I：

10.1016/j.tet.2004.06.114

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Norbornene derivatives bearing endo-substituents in the 5- and 6-positions were studied as substrates for ene-yne metathesis cascades. Substrates which contained an internal alkyne and a terminal alkene or alkyne in each sidechain were found to undergo a metathesis cascade leading to pentacyclic bis-dienes and bis-trienes. Attempts to extend the chemistry further to sidechains containing two internal alkynes or two internal alkynes and a terminal alkene were not successful with the first generation Grubbs' catalyst. However, the substrate containing two internal alkynes did react with the second generation Grubbs' catalyst to give a tetra-diene containing product. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：8043 / 8052

页数：10

共 38 条

[1] Control of product distribution in the domino metathesis reactions of N-alkynyl 2-azabicyclo[2.2.1]hept-5-en-3-ones.: A convenient synthesis of functionalized γ-lactams and indolizidinones [J].