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(Z)-Trifluoromethyl-Trisubstituted Alkenes or Isoxazolines: Divergent Pathways from the Same Allene.

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Because of a charge-dipole interaction involving nonbonding electron pairs on fluorine, protonation of trifluoromethyl allenes leads to tri- or tetrasubstituted alkenes with high (Z)-selectivity. Treatment of the same allenes with… Click to show full abstract

Because of a charge-dipole interaction involving nonbonding electron pairs on fluorine, protonation of trifluoromethyl allenes leads to tri- or tetrasubstituted alkenes with high (Z)-selectivity. Treatment of the same allenes with catalytic Au(I) initiates a reaction cascade that produces isoxazolines in high yield.

Keywords: pathways allene; alkenes isoxazolines; trisubstituted alkenes; isoxazolines divergent; divergent pathways; trifluoromethyl trisubstituted

Journal Title: Organic letters
Year Published: 2020

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