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.
Unusual Non-Oxidative Pummerer Rearrangement of gamma-Trifluoro-beta-aminosuifoxides
CRUCIANELLI, MARCELLO;
1995-01-01
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.File in questo prodotto:
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