Stereoselective synthesis of Z alkenyl halides via Julia olefination.
Julia olefination between alpha-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.
Lebrun
Marie-Eve
ME
Department of Medicinal Chemistry, Merck Frosst Centre for Therapeutic Research, Post Office Box 1005, Pointe-Claire/Dorval, Québec H9R 4P8, Canada.
Le Marquand
Paul
P
Berthelette
Carl
C
D000447:Aldehydes / Q000737:chemistry; D000475:Alkenes / Q000138:chemical synthesis*; D001965:Bromides / Q000138:chemical synthesis*; D002712:Chlorides / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013450:Sulfones / Q000138:chemical synthesis / Q000737:chemistry
D000447:Aldehydes; D000475:Alkenes; D001965:Bromides; D002712:Chlorides; D013450:Sulfones