A General Process for Synthesis of Enantiopure Sulfinates and Sulfoxides

chiral sulfoxides - organomagnesium reagents - sulfinates

Significance

Among various methods, developed for the synthesis of enantiopure sulfoxides, the use of naturally occurring quinine as a chiral auxiliary has a lot of advantages: all the reagents are easily available, cheap, the one-pot procedure is very simple to perform and the auxiliary can be readily recovered. The procedure gives in all reported cases practically enantiopure products.

Comment

In most syntheses of enantiopure sulf­oxides from organometallic species, the enantio­selectivity is based on the difference between two S-Y (Y = O or N) enantiotopic bonds. The originality of this approach relays on the formation of a non-covalent S-N bond as enantiotopic for an easily available quinine derivate, that allowed practically complete stereocontrol in the reaction with organometallic reagents.