✦ LIBER ✦
Preparation of optically active stilbene oxides via sulfonium salts derived from C2 symmetric thiolanes.
✍ Scribed by L. Breau; W.W. Ogilvie; T. Durst
- Book ID
- 104226447
- Publisher
- Elsevier Science
- Year
- 1990
- Tongue
- French
- Weight
- 243 KB
- Volume
- 31
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Trans-stilbene oxides have been obtained in up to 83% enantiomeric excess via reaction of S-benzyl ylides prepared from optically active trans-2,5disubstituted thiolanes. The potential of sulfur ylides for the preparation of optically active epoxides was first recognized and investigated by Trost and Hammen in 1973.2 Unfortunately their system, reaction of the ylide from optically active adamantylethylmethylsulphonium tetrafluoroborate with benzaldehyde, yielded styrene oxide with essentially no enantiometic excess.