Calcium(II)- and Triflimide-Catalyzed Intramolecular
Hydroacyloxylation of Unactivated Alkenes in Hexafluoroisopropanol
Posted on 2019-09-05 - 13:33
We report an efficient
intramolecular hydroacyloxylation of unactivated
alkenes, offering a streamlined access to relevant γ-lactones,
which features the utilization of either a calcium(II) salt or triflimide
as a catalyst in hexafluoroisopropanol. This method could be applied
to the synthesis of natural products and the late-stage functionalization
of natural and bioactive molecules. Additionally, DFT computations
were used to elucidate the twist of reactivity observed between the
hydroamidation and hydroacyloxylation of unactivated alkenes regarding
the formation of 5- and 6-membered rings.
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Qi, Chenxiao; Yang, Shengwen; Gandon, Vincent; Lebœuf, David (2019). Calcium(II)- and Triflimide-Catalyzed Intramolecular
Hydroacyloxylation of Unactivated Alkenes in Hexafluoroisopropanol. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.9b02705
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AUTHORS (4)
- CQChenxiao QiSYShengwen YangVGVincent GandonDLDavid Lebœuf
KEYWORDS
6- membered ringshydroacyloxylationintramolecularcomputationhydroamidationHexafluoroisopropanolAlkeneutilizationTriflimide-Catalyzed Intramolecular Hydroacyloxylationaccessreactivityunactivated alkeneselucidatefunctionalizationlactonemethodsynthesishexafluoroisopropanolUnactivatedofferingDFTmoleculeCalciumformationcatalyst5-bioactivecalciumtriflimideγ-late-stage