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Article

Stereoselective Synthesis of Z Alkenyl Halides via Julia Olefination

Supporting Info

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, Qubec H9R 4P8, Canada

J. Org. Chem., 2006, 71 (5), pp 2009–2013

DOI: 10.1021/jo052370h

Publication Date (Web): January 31, 2006

To whom correspondence should be addressed. Phone: (514) 428-3359. Fax: (514) 428-4900.

, carl_berthelette@merck.com

Abstract

Julia olefination between α-halomethyl sulfones and a variety of aldehydes afforded alkenyl halides in good to excellent yields with high E/Z stereoselectivities. Sulfones were readily prepared in two or three steps from commercially available reagents in good yields. Optimization revealed that the nature of the solvent, the base, and the additive were crucial to obtain the desired alkenyl halides.

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Published In Issue March 03, 2006
Received November 16, 2005

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Article

Stereoselective Synthesis of Z Alkenyl Halides via Julia Olefination

Abstract

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SciFinder Links

History

Recommend & Share

Related Content

3,5-Bis(trifluoromethyl)phenyl Sulfones in the Direct Julia−Kocienski Olefination

Total Synthesis of (−)-Acutumine

Improved Julia−Kocienski Conditions for the Methylenation of Aldehydes and Ketones

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