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Issue 8, 2019
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Chiral phosphoric acid-catalyzed asymmetric C(sp3)–H functionalization of biomass-derived 2,5-dimethylfuran via two sequential Cope-type rearrangements

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Abstract

Reported herein is the first organocatalytic asymmetric C(sp3)–H functionalization of biomass-derived 2,5-dimethylfuran with 3-hydroxy-3-indolyoxindoles to afford enantioenriched furan-derived 3,3′-disubstituted oxindoles in high enantioselectivity. This reaction is realized through chiral acid-catalyzed two sequential Cope-type rearrangements as proved by DFT calculations, which demonstrates a strategically new reactivity of 2,5-dimethylfuran, enabling the direct production of chiral chemicals from biomass-derived molecules.

Graphical abstract: Chiral phosphoric acid-catalyzed asymmetric C(sp3)–H functionalization of biomass-derived 2,5-dimethylfuran via two sequential Cope-type rearrangements

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Publication details

The article was received on 19 Dec 2018, accepted on 25 Feb 2019 and first published on 26 Feb 2019


Article type: Research Article
DOI: 10.1039/C8QO01375F
Org. Chem. Front., 2019,6, 1162-1167

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    Chiral phosphoric acid-catalyzed asymmetric C(sp3)–H functionalization of biomass-derived 2,5-dimethylfuran via two sequential Cope-type rearrangements

    L. Xu, H. Chen, J. Liu, L. Zhou, Q. Liu, Y. Lan and J. Xiao, Org. Chem. Front., 2019, 6, 1162
    DOI: 10.1039/C8QO01375F

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