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Synlett 1996; 1996(3): 249-251
DOI: 10.1055/s-1996-5371
DOI: 10.1055/s-1996-5371
letter
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Enantioselective Pummerer-Type Rearrangement of γ-Fluoro-β-Enaminosulfoxides: Efficient Approach to Chiral Non-Racemic α,α-N,S-Disubstituted Ketals of β-Fluoro-Pyruvaldehydes
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Publication History
Publication Date:
31 December 2000 (online)
The enantioselective synthesis of chiral non-racemic α,α-N,S-disubstituted ketals of β-fluoro-pyruvaldehydes 2 has been efficiently accomplished by one-pot treatment of the γ-fluoro-β-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.
fluoropyruvaldehydes - Pummerer rearrangement - enantioselective - trifluoroacetic anhydride - ketals