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EnglishThe enantioselective synthesis of chiral non-racemic alpha,alpha-N,S-disubstituted ketals of beta-fluoro-pyruvaldehydes 2 has been efficiently accomplished by one-per treatment of the gamma-fluoro-beta-enaminosulfoxides 1 with trifluoroacetic anhydride and then with silica gel. Two fast and enantioselective rearrangements should be involved in the reaction. A change of reaction conditions or the use of other promoters, like acyl chlorides, can produce achiral vinyl sulfides.
http://hdl.handle.net/11697/11681| Titolo: | Enantioselective pummerer-type rearrangement of gamma-fluoro-beta-enaminosulfoxides: Efficient approach to chiral non-racemic alpha,alpha-N,S-disubstituted ketals of beta-fluoro-pyruvaldehydes |
| Autori interni: | CRUCIANELLI, MARCELLO |
| Data di pubblicazione: | 1996 |
| Rivista: | SYNLETT |
| Abstract: | The enantioselective synthesis of chiral non-racemic alpha,alpha-N,S-disubstituted ketals of beta-fluoro-pyruvaldehydes 2 has been efficiently accomplished by one-per treatment of the gamma-fluoro-beta-enaminosulfoxides 1 with trifluoroacetic anhydride and then with silica gel. Two fast and enantioselective rearrangements should be involved in the reaction. A change of reaction conditions or the use of other promoters, like acyl chlorides, can produce achiral vinyl sulfides. |
| Handle: | http://hdl.handle.net/11697/11681 |
| Appare nelle tipologie: | 1.1 Articolo in rivista |
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