Sulfides sulfinimines

Tietze and Schuffenhauer explored the intermolecular hetero Diels-Alder reaction of ethyl vinyl ether and sulfinimine 204 and found that at high pressures (11 kbar) and long reaction times (48 h at room temperature), tetrahydropyridines 205 and 206 were obtained in 96% yield and in a ratio of 1.7 1.107 The exo-adducts were not observed. Phenyl vinyl sulfide reacts similarly, but simple alkenes failed. Theoretical calculations and the experimental results suggest that while the cycloaddition is concerted, it is highly asynchronous. 

N-Sulfonyloxaziridines are an important class of selective, neutral, and aprotic oxidizing reagents.11 Enantiopure N-sulfonyloxaziridines have been used in the asymmetric hydroxylation of enolates to enantiomerically enriched a-hydroxy carbonyl compounds,9 11-13 the asymmetric oxidation of sulfides to sulfoxides,14 1S selenides to selenoxides,16 sulfenimines to sulfinimines,17 and the epoxidation of alkenes.18... 

The availability of f j-di-r-butyl disulfide monoxide from selective oxidation catalyzed by vanadyl-88 enables the preparation of chiral r-butyl sulfinamides, sulfoxides, and sulfinimines. Very similar reaction conditions bring about the transformation of various 1,3-dithianes to chiral monoxides. (/ ,Rl-2,2,5,5-Tetramethyl-3,4-hexanediol is a chiral ligand for the Ti(IV)-catalyzed oxidation of sulfides with cumene hydroperoxide. ... 

Andere Diaryl-, Dialkyl- und Alkyl-aryl-sulfinimine lassen sich in Gegenwart etwas ge-ringerer Katalysatormengen in Sulfide uberfiihren. Eine Spaltung der C-S- oder N—SOi-Bindung tritt nicht ein1,2. 

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