Conversion of γ-substituted bicyclo[2.2.1] (Z)-vinylsulfones to the corresponding (E)-allylsulfones

The preparation of bicyclo[2.2.1] (E)-allylsulfones starting from the corresponding (Z)-vinylsulfones is described. Starting from 2,3-bis(phenylsulfonyl)norbornadiene 1, the Michael addition of organometallic reagents followed by the base catalyzed isomerization affords (E)-allylsulfones in high yields. The procedure allows to obtain vinylidenic norbornenes which are characteristic nuclei of valuable biologically active compounds.

Graphical abstractThe preparation of a series of bicyclo[2.2.1] (E)-allylsulfones starting from the corresponding (Z)-vinylsulfones is described. The procedure affords valuable vinylidenic norbornenes, characteristic nuclei of biologically active compounds.Download full-size image