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Stereoselective Synthesis of Z Alkenyl Halides via Julia Olefination

Marie-Eve Lebrun, Paul Le Marquand and Carl Berthelette*

*Department of Medicinal Chemistry, Merck Frosst Centre for Therapeutic Research, Post Office Box 1005, Pointe-Claire/Dorval, Québec H9R 4P8, Canada, Email:

M.-E. Lebrun, P. Le Marquand, C. Berthelette, J. Org. Chem., 2006, 71, 2009-2013.

DOI: 10.1021/jo052370h


An optimized Julia olefination between readily available α-halomethyl sulfones and a variety of aldehydes afforded alkenyl halides in good to excellent yields with high E/Z stereoselectivities.

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Key Words

modified Julia Olefination, alkenyl halides

ID: J42-Y2006-640