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.
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: | ||
Data di pubblicazione: | 1996 | |
Rivista: | ||
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 |
File in questo prodotto:
Non ci sono file associati a questo prodotto.
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.