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EnglishTrifluoroacetic anhydride promoted Pummerer rearrangement of gamma-trifluoro-beta-amino sulfoxides 1 follows an unusual pathway, in which a migration of the p-tolylthio group to the nitrogen atom provides the corresponding a-sulfenamidotriflnoroacetates 5. The usual removal of the proton in o~ to the sulfinyl moiety does not take place, as shown by maintenance of deuterium during the rearrangement. This procedure is exploited for the stereoselective synthesis of 2D- and 2H- (R)-2- amino-3,3,3-trifluoropropan- 1-ol 10.
http://hdl.handle.net/11697/2338| Titolo: | Unusual Non-Oxidative Pummerer Rearrangement of gamma-Trifluoro-beta-aminosuifoxides |
| Autori interni: | CRUCIANELLI, MARCELLO |
| Data di pubblicazione: | 1995 |
| Rivista: | TETRAHEDRON LETTERS |
| Abstract: | Trifluoroacetic anhydride promoted Pummerer rearrangement of gamma-trifluoro-beta-amino sulfoxides 1 follows an unusual pathway, in which a migration of the p-tolylthio group to the nitrogen atom provides the corresponding a-sulfenamidotriflnoroacetates 5. The usual removal of the proton in o~ to the sulfinyl moiety does not take place, as shown by maintenance of deuterium during the rearrangement. This procedure is exploited for the stereoselective synthesis of 2D- and 2H- (R)-2- amino-3,3,3-trifluoropropan- 1-ol 10. |
| Handle: | http://hdl.handle.net/11697/2338 |
| Appare nelle tipologie: | 1.1 Articolo in rivista |
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