Sulfoximines carbonyl epoxidation

Like S,S-Dimethyl-N-(p-toluenesulfonyl)sulfoximine and (dimethylamino)dimethyloxosulfonium tetrafluoroborate, the 7Y-tosylsulfilimine (1) reacts as a methylene transfer reagent, converting aldehydes and ketones to epoxides (eq 3). Thus (1) is heated at 80-90 °C for 0.5 h in DMSO in the presence of Sodium Hydride, and the resulting anion is allowed to react with carbonyl compounds to give 1-mono- and 1,1-disubstituted oxiranes in 46-56% yields. ... 

The few published attempts at the asymmetric epoxidation of carbonyl compounds with chiral sulfur ylides have been reviewed. Thus far, such processes have not been very useful synthetically. For example, reaction of benzaldehyde with an optically pure sulfoximine ylide only afforded an qioxide in 20% enantiomeric excess. More recently, chiral sulfur methylides have provided tra/i -stilbene oxides in up to 83% ee An example of optical induction observed in reactions t ng place with a chiral phase transfer reagent was reported, but later disputed. ... 

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