Reductive elimination hydroxy sulfoximines

Reductive elimination of (3-hydroxy sulfoximines with aluminum amalgam in acetic acid gives alkenes in good yields.70In one study, the resolved carbinol adducts of the ketone 93 and (+)-(S)-2b were individually treated with aluminum amalgam in acetic acid to give natural (-)-(3-panasinsene and its antipode in high enantiomeric purity.71... 

Methylenation of carbonyl compounds. The reagent reacts with aldehydes and ketones in THF at 0° to give 0-hydroxy sulfoximines (2). On reduction of (2) with aluminum amalgam in aqueous THF containing acetic acid, reductive elimination occurs to give an olefin (3). 

Unfortunately, reductive elimination of diastereoisomerically pure )S-hydroxy-sulfoximines leads to mixtures of ( )- and (Z)-alkenes (Table 3.16) [152]. In general, the elimination of sulfoximines is less trans-selective [3,152]. 

---