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Catalytic asymmetric trifluoromethylthiolation via enantioselective [2,3]-sigmatropic rearrangement of sulfonium ylides

10:10 EDT 6 Jun 2017 | Nature Publishing

The asymmetric Doyle-Kirmse reaction using chiral Rh(II)- or Cu(I)-catalysts provides SCF3-containing compounds in highly efficient and enantioselective manner. The reaction proceeds through enantioselective formation of sulfonium ylide from a diazoester and allyl- or propargyl trifluoromethyl sulfide, followed by concerted [2,3]-sigmatropic rearrangement with the transfer of chirality from sulfur to carbon.

Original Article: Catalytic asymmetric trifluoromethylthiolation via enantioselective [2,3]-sigmatropic rearrangement of sulfonium ylides

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