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Asymmetric synthesis of dihydrocoumarins via the organocatalytic hetero-Diels–Alder reaction of ortho-quinone methides

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Abstract

Enantioselective organocatalytic inverse-electron-demand hetero-Diels–Alder reactions of in situ generated ortho-quinone methides with azlactones have been developed. This strategy could generate various chiral dihydrocoumarins bearing a quaternary amino acid moiety in high yields (up to 94%) and stereoselectivities (up to 99 : 1 e.r., >20 : 1 dr) in the presence of a chiral phosphoric acid catalyst. The useful transformation and mechanistic study of this process are also presented.

Graphical abstract: Asymmetric synthesis of dihydrocoumarins via the organocatalytic hetero-Diels–Alder reaction of ortho-quinone methides

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Publication details

The article was received on 18 Sep 2017, accepted on 29 Sep 2017 and first published on 29 Sep 2017


Article type: Paper
DOI: 10.1039/C7OB02325A
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Asymmetric synthesis of dihydrocoumarins via the organocatalytic hetero-Diels–Alder reaction of ortho-quinone methides

    L. Zhang, Y. Liu, K. Liu, Z. Liu, N. He and W. Li, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB02325A

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