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ChemInform Abstract: A Highly Stereoselective, Modular Route to (E)-Vinylsulfones and to (Z)- and (E)-Alkenes.

โœ Scribed by Marie-Gabrielle Braun; Beatrice Quiclet-Sire; Samir Z. Zard

Publisher
John Wiley and Sons
Year
2012
Weight
71 KB
Volume
43
Category
Article
ISSN
0931-7597

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โœฆ Synopsis

The title method is based on the recently discovered radical fragmentation of 2-fluoro-6-pyridinoxy derivatives of vinylsulfones. The radical addition of xanthates to these alkenes leads to the formation of (E)-vinylsulfone adducts, which are desulfonylated by treatment with sodium dithionite and sodium bicarbonate to give the desired (Z)-alkenes. Desulfonylation using sodium amalgam provides the corresponding (E)-alkenes. The method can be applied to modify side chains of steroids bearing either the vinylsulfone or the xanthate moiety. -(BRAUN, M.-G.; QUICLET-SIRE,

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