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Asymmetric Diels–Alder cycloadditions of benzofulvene-based 2,4-dienals via trienamine activation

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Abstract

A new type of 2,4-dienal with α-substitutions and featuring a benzofulvene skeleton has been designed and utilised in asymmetric Diels–Alder cycloaddition reactions with 3-olefinic oxindoles under the trienamine catalysis of a chiral secondary amine. An array of chiral polyhydrofluorene frameworks with complex molecular structures are constructed efficiently, generally in fair to high yields with good diastereoselectivity and excellent enantioselectivity.

Graphical abstract: Asymmetric Diels–Alder cycloadditions of benzofulvene-based 2,4-dienals via trienamine activation

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Publication details

The article was received on 02 Jul 2018, accepted on 07 Aug 2018 and first published on 08 Aug 2018


Article type: Research Article
DOI: 10.1039/C8QO00653A
Citation: Org. Chem. Front., 2018, Advance Article
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    Asymmetric Diels–Alder cycloadditions of benzofulvene-based 2,4-dienals via trienamine activation

    J. Yue, G. Ran, X. Yang, W. Du and Y. Chen, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C8QO00653A

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