Single-Isomer Tetrasubstituted Olefins from Regioselective and Stereospecific Palladium-Catalyzed Coupling of β-Chloro-α-iodo-α,β-unsaturated Esters

Alison B. Lemay, Katarina S. Vulic, and William W. Ogilvie*
Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Ontario, Canada K1N 6N5 %wogilvie@science.uottawa.ca
J. Org. Chem., 2006, 71 (9), pp 3615–3618
DOI: 10.1021/jo060144h
Publication Date (Web): March 28, 2006
Copyright © 2006 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

Abstract Image

The efficient regioselective and stereospecific synthesis of tetrasubstituted olefins using a mild and convenient method is disclosed. 2-Alkynyl esters are selectively converted to E-β-chloro-α-iodo-α,β-unsaturated esters by exposure to Bu4NI in refluxing dichloroethane. These products are produced cleanly, regio- and stereoselectively, and in high yields. Single-isomer tetrasubstituted olefins bearing four different carbon substituents are then synthesized by sequential palladium-catalyzed coupling reactions. Selectivity results from reactivity differences in the intermediate substrates.

View: Full Text HTML | Hi-Res PDF

Tools

History

  • Published In Issue April 28, 2006
  • Received January 23, 2006

Recommend & Share

Related Content

Other ACS content by these authors: