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Issue 44, 2019
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3-Nitro-3,4-dihydrocoumarins: valuable precursors for the synthesis of enantiomerically enriched masked quaternary α-amino acid derivatives with a 3,4-dihydrocoumarin scaffold

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Abstract

A bifunctional squaramide catalyzed enantioselective formal [2 + 4] annulation reaction with 3-nitro-3,4-dihydrocoumarins and ortho-quinone methide has been developed. Novel chiral masked quaternary α-amino acid derivatives with a 3,4-dihydrocoumarin scaffold are obtained in a highly stereocontrolled manner. Representative transformation of the annulation product to a biologically important quaternary α-amino acid derivative is achieved without any appreciable loss in the diastereo- and enantioselectivity.

Graphical abstract: 3-Nitro-3,4-dihydrocoumarins: valuable precursors for the synthesis of enantiomerically enriched masked quaternary α-amino acid derivatives with a 3,4-dihydrocoumarin scaffold

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Publication details

The article was received on 26 Sep 2019, accepted on 22 Oct 2019 and first published on 24 Oct 2019


Article type: Paper
DOI: 10.1039/C9OB02089F
Org. Biomol. Chem., 2019,17, 9636-9645

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    3-Nitro-3,4-dihydrocoumarins: valuable precursors for the synthesis of enantiomerically enriched masked quaternary α-amino acid derivatives with a 3,4-dihydrocoumarin scaffold

    D. Lv, M. Zhao, Y. Wang and Z. Zhou, Org. Biomol. Chem., 2019, 17, 9636
    DOI: 10.1039/C9OB02089F

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