3-Oxo-[1,3λ6,4]-oxathiazines: A Novel Class of Heterocyclic S,O-Acetals
Michael Reggelin reports on a new class of heterocyclic S,O-acetals.
About 30 years ago, in an attempt to prepare enantiomerically pure sulfonimidoylfluorides, Professor Michael Reggelin of the Technische Universität Darmstadt (Germany) serendipitously synthesized the first cyclic sulfonimidates. Since that initial discovery, both S-epimeric compounds and derivatives thereof have proven to be valuable starting materials for the synthesis of enantiomerically pure sulfoximines in general and 2-alkenyl sulfoximines in particular.
In this study, the authors used two different methods of a novel class of heterocyclic diastereo- and enantiopure S,O-acetals – one involving a chemoselective monohalogenation of sulfoximines, the other starting with a stereoselective ring opening of sulfonimidates with a carbenoid as the key step. The base-induced cyclization of the S-(halomethyl)sulfoximine intermediates resulted in the formation of 3-oxo-[1,3λ6,4]-oxathiazines.
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