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.
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
CRUCIANELLI, MARCELLO;
1996-01-01
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.File in questo prodotto:
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