Preparation of α-ethylenic ketene dithioacetals from α-oxoketene dithioacetals.
✍ Scribed by Serge Masson; André Thuillier
- Publisher
- Elsevier Science
- Year
- 1980
- Tongue
- French
- Weight
- 146 KB
- Volume
- 21
- Category
- Article
- ISSN
- 0040-4039
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📜 SIMILAR VOLUMES
a-Ox0 ketene dithioacetals can be converted into a-pyrones in a three step process involving 1,2-nucleophilic addition of ester or ketone enolate anions, acid promoted rearrangement, and subsequent en01 lactonization. Utilization of ester enolates affords 6-alkylthio a-pyrones while ketone enolates
The chemoselective and stereoselective addition of organocuprates to cyclic a-oxoketene dithioacetals affords predominately the E vinylogous thioesters. An acyclic a-oxoketene dithioacetal affords the 2 vinylogous thioester stereoselectively. The observed selectivities are dependent upon substrate