ol9b01831_si_001.pdf (7.58 MB)
Stereoselective β–F Elimination Enabled Redox-Neutral [4 + 1] Annulation via Rh(III)-Catalyzed C–H Activation: Access to Z‑Monofluoroalkenyl Dihydrobenzo[d]isoxazole Framework
journal contribution
posted on 2019-06-26, 11:39 authored by Hui Gao, Ming Sun, Haiman Zhang, Mengyao Bian, Min Wu, Guoxun Zhu, Zhi Zhou, Wei YiAn
efficient and practical Rh(III)-catalyzed redox-neutral [4 +
1] annulation of N-phenoxy amides with α,α-difluoromethylene alkynes has been realized
to give direct access to the Z-configured monofluoroalkenyl
dihydrobenzo[d]isoxazole framework with broad substrate
compatibility and good functional group tolerance, which was further
enhanced by the late-stage C–H modification of complex bioactive
compounds. Subsequent density functional theory calculations revealed
that the stereoselective β–F elimination involving an
allene species played a decisive role in determining the reaction
outcome and such Z-selectivity.
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Annulationisoxazole FrameworkAccessDihydrobenzophenoxy amidesRhaccessdihydrobenzoActivationannulationRedox-Neutralrolesubstrate compatibilitystereoselectiveEliminationallene speciesconfiguredmonofluoroalkenyldifluoromethylene alkynesbioactive compoundsEnabledreaction outcomeframeworktheory calculationsSubsequent densityeliminationgroup toleranceselectivityStereoselectiveMonofluoroalkenylredox-neutralmodificationlate-stage
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