Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 88, Issue 23, Pages 16330-16339Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.3c01840
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Bridged isoxazolidines were synthesized via Rh-(III)-catalyzed C-H allylation of alpha-aryl nitrones with 5-methylene-1,3-dioxan-2-one. The nitrone group acted as a directing group and 1,3-dipole in the C-H activation/[3 + 2] cycloaddition cascade, showing excellent chemo- and stereoselectivity as well as good functional group compatibility. The resulting compounds' skeletal structure could be conveniently modified and applied in the synthesis of biologically active molecules.
Bridged isoxazolidines were synthesized via Rh-(III)-catalyzed C-H allylation of alpha-aryl nitrones with 5-methylene-1,3-dioxan-2-one. The nitrone group serves as a directing group and 1,3-dipole in the C-H activation/[3 + 2] cycloaddition cascade, exhibiting excellent chemo- and stereoselectivity along with good functional group compatibility. The resulting skeletal structure was conveniently modified to produce a range of important chemical frameworks, and the protocol was applied to biologically active molecules.
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