ol0c01357_si_001.pdf (13.42 MB)
Organocatalytic Approach for Assembling Flavanones via a Cascade 1,4-Conjugate Addition/oxa-Michael Addition between Propargylamines with Water
journal contribution
posted on 2020-05-22, 10:29 authored by Xinwei He, Mengqing Xie, Ruxue Li, Pui Ying Choy, Qiang Tang, Yongjia Shang, Fuk Yee KwongA DBU-catalyzed
one-pot cascade reaction of propargylamines and
water for the synthesis of flavanones has been developed. This process
proceeds via a sequence of 1,4-conjugate addition of water to alkynyl o-quinone methide (o-AQM), followed by
the alkyne–allene isomerization and subsequent intramolecular oxa-Michael addition. This strategy provides a convenient
method for accessing a broad range of flavanones in good to excellent
yields with good functional-group tolerance, in particular, the reactive
halo functional groups.
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Michael Additionsequencefunctional-group toleranceaccessingconjugatepropargylaminestrategyintramolecular oxaalkynylAQMquinone methideAssembling FlavanonesmethodsynthesisOrganocatalytic ApproachyieldCascadeflavanonereactive haloMichael additionDBU-catalyzed one-pot cascade reactionalkyneprocess proceedsConjugateisomerizationPropargylamine
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