Ruthenium-carbene complex catalyzed cross metathesis of monoallyl α-, β-, and γ-cyclodextrins with perfluoroalkylpropenes resulted in the formation of the corresponding perfluoroalkylated cyclodextrins. The reactions proceeded under standard reaction conditions and yielded the desired
Three types of brassinosteroid analogues with perfluoroalkylated side chains were synthesized by using alkene cross-metathesis of a brassinosteroid derivative bearing a terminal alkene moiety with different (perfluoroalkyl)propenes. The presence of the double bonds in the cross-metathesis products allowed a facile one-step double dihydroxylation to provide intermediates that after Baeyer-Villiger oxidation afforded the target compounds. Biological activity of the prepared analogues was tested in GABA(A) receptor, cytotoxic, and brassinolide activity, which reached in some cases the same range as their nonfluorinated analogues.
A new approach to perfluoroalkylated compounds based on cross-metathesis between perfluoropropenes and terminal alkenes has been developed. The reaction is catalysed with high efficiency and selectivity by the Hoveyda-Grubbs second-generation catalyst under mild reaction conditions. The
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