Journal
ORGANIC LETTERS
Volume 21, Issue 13, Pages 5229-5233Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b01831
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Funding
- NSFC [21877020]
- Guangdong Natural Science Funds for Distinguished Young Scholar [2017A030306031]
- Natural Science Foundation of Guangdong Province [2017A030313058]
- National College Students' Innovation Training Program [2017A085, 201810570020]
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An efficient and practical Rh(III)-catalyzed redox-neutral [4 + 1] annulation of N-phenoxy amides with alpha,alpha-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 beta-F elimination involving an allene species played a decisive role in determining the reaction outcome and such Z-selectivity.
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