Diastereoselective formation of 5-vinylcyclopentenes from 1,6-enynes: Cobalt-mediated C-H allylic activation and formal 5-endo-dig cyclization

Authors
Dolaine, R Gleason, JL
Citation
R. Dolaine et Jl. Gleason, Diastereoselective formation of 5-vinylcyclopentenes from 1,6-enynes: Cobalt-mediated C-H allylic activation and formal 5-endo-dig cyclization, ORG LETT, 2(12), 2000, pp. 1753-1756
Citations number
27
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
12
Year of publication
2000
Pages
1753 - 1756
Database
ISI
SICI code
1523-7060(20000615)2:12<1753:DFO5F1>2.0.ZU;2-B
Abstract
[GRAPHICS] A novel intramolecular cyclization reaction mediated by dicobalt octacarbon yl (Co-2(CO)(8)) is reported. Thermolysis in an argon atmosphere transforms the cobalt complex of 1-trimethyisilyl-6-hepten-1-ynes into 1-trimethylsil yl-5-vinylcyclopentenes in good yield and in a highly diastereoselective ma nner. This formal 5-endo-dig cyclization is proposed to proceed via an ally lic C-H oxidative addition.