Org. Lett., 2 (12), 1709 -1712, 2000. 10.1021/ol000064e S1523-7060(00)00064-X
Web Release Date: May 17, 2000

Copyright © 2000 American Chemical Society

,-Epoxy Vinyl Triflates in Pd-Catalyzed Reactions

Kana Yamamoto and Clayton H. Heathcock*

Department of Chemistry, University of California, Berkeley, Berkeley, California, 94720-1460

chh@steroid.cchem.berkeley.edu

Received March 23, 2000

Abstract:

Reactions of steroidal ,-epoxy vinyl triflates in Pd-catalyzed reactions are described. Oxidative insertion of Pd⁰ into the C-O bond, giving vinylpalladium 12, is faster than formation of the -allyl derivative from the vinyl epoxide. Although 12 can be trapped under certain conditions, it eventually rearranges to palladium alkoxide 14, which is in equilibrium with 15 and/or 10.

---

Download the full text: PDF | HTML