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DOI: 10.1055/s-2005-869930
A General Process for Synthesis of Enantiopure Sulfinates and Sulfoxides
Contributor(s): Paul Knochel, Andrei GavryushinPublication History
Publication Date:
20 July 2005 (online)
Key words
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.