Sulfoximines

Sulfoximines

The discovery in 1988: A caclic sulfonimidate as starting material for enantiomerically pure sulfoximines
The discovery in 1988: A caclic sulfonimidate as starting material for enantiomerically pure sulfoximines

Since their discovery in the early 1950’s sulfoximines have developed to a powerful tool in organic synthesis.[Review] This is especially true for the chiral non-racemic members of this uncommonly versatile class of compounds. Early work focused on the development of asymmetric alkylidene transfer reagents and ketone resolutions based on the reversible formation of β-hydroxy-sulfoximines. Nowadays sulfoximine chemistry is characterized by a transition from stoichiometric to catalytic applications. Cyclic sulfonimidates 1 [1,2,3] have proven to be valuable intermediates for the synthesis of enantiomerically pure sulfoximines. These compounds can be elaborated further into chiral ligands for asymmetric metal catalyzed reactions[4,5] and are the basis for asymmetric allyl transfer reagents.[6,7] The latter application relies on metallated 2-alkenylsulfoximines which, after diastereoselective γ-hydroxyalkylation, can be cyclized to yield isomerically pure highly substituted N- and O-heterocyclic systems.[8,9,10,11]
After removal of the auxiliary these compounds may have significance as β-turn mimetica or can be used as building blocks in natural product synthesis. Desulfuration is possible either by reduction with Raney-nickel or samarium iodide.