alpha,beta-Epoxy vinyl triflates in Pd-catalyzed reactions

Authors
Yamamoto, K Heathcock, CH
Citation
K. Yamamoto et Ch. Heathcock, alpha,beta-Epoxy vinyl triflates in Pd-catalyzed reactions, ORG LETT, 2(12), 2000, pp. 1709-1712
Citations number
29
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
12
Year of publication
2000
Pages
1709 - 1712
Database
ISI
SICI code
1523-7060(20000615)2:12<1709:AVTIPR>2.0.ZU;2-S
Abstract
[GRAPHICS] Reactions of steroidal alpha,beta-epoxy vinyl triflates in Pd-catalyzed rea ctions are described. Oxidative insertion of Pd-0 into the C-O bond, giving vinylpalladium 12, is faster than formation of the pi-allyl derivative fro m the vinyl epoxide. Although 12 can be trapped under certain conditions, i t eventually rearranges to palladium alkoxide 14, which is in equilibrium w ith 15 and/or 10.