(Z)-Trifluoromethyl-Trisubstituted Alkenes or Isoxazolines: Divergent Pathways from the Same Allene
Chaolun Liu1, Glenn P A Yap2, Casey A Rowland2
1Chemistry Department, University of Hawaii at Manoa, 2545 The Mall, Honolulu, Hawaii 96822, United States.
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.
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