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, Email: wogilviescience.uottawa.ca

A. B. Lemay, K. S. Vulic, W. W. Ogilvie, J. Org. Chem., 2006, 71, 3615-3618.

DOI: 10.1021/jo060144h

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Abstract

2-Alkynyl esters are stereo- and regioselectively converted to E-β-chloro-α-iodo-α,β-unsaturated esters by exposure to Bu₄NI in refluxing dichloroethane. Single-isomer tetrasubstituted olefins bearing four different carbon substituents are then synthesized by sequential palladium-catalyzed coupling reactions.

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Key Words

Vinyliodides, Vinylchlorides, Enynes, Sonogashira Coupling, Suzuki Coupling, 1,3-dienes

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ID: J42-Y2006-1170