Vinylogous trifluoromethyl

The naturally occurring sulfonamide (-)-altemicidin is the first 6-azaindene monoterpene alkaloid isolated as a metabolite of microorganisms. A.S. Kende utilized the Polonovski-Potier reaction in the key step to introduce the carbamoyl enamine functionality. The tertiary amine was oxidized to the A/-oxide by H2O2 followed by treatment with excess TFAA to afford the desired vinylogous trifluoromethyl amide. 

Vinylogous trifluoromethyl amides. The Potier-Polonovski rearrangement of tertiary amine A(-oxides induced by (CFjCOjjO is frequently followed by trifluoroacetylation. This method is most suitable for the synthesis of (-)-altemicidin. ... 

L2909>. An organocatalytic addition of 2-trimethylsilyloxyfuran to aldehydes using 10 mol% of l,3-bis(3-(trifluoromethyl)phenyl)urea provided adducts with modest threo selectivity <06TL8507>. A syn-selective, enantioselective, organocatalytic vinylogous Mukaiyama-Michael addition of 2-trimethylsilyloxyfuran to (E)-3-... 

In the presence of triethylamine, enaminones 11 are synthesized in high yields from the corresponding amino ester or amino nitrite hydrochlorides and vinylogous esters 10, Scheme 4 (89TL6173, 92S533). The products are precursors for trifluoromethyl-substituted pyrroles and dihydropyrroles (Section V,C). 

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