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Issue 30, 2018
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Highly efficient synthesis of benzodioxins with a 2-site quaternary carbon structure by secondary amine-catalyzed dual Michael cascade reactions

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Abstract

Salicylic acids and substituted ynones were employed as substrates to afford a class of valuable 4H-benzo[d][1,3]dioxin-4-ones with a 2-site quaternary carbon structure in up to 92% yield by secondary amine-catalyzed dual Michael cascade reactions under mild reaction conditions. The α,β-unsaturated ketone as the key intermediate in the cascade process was successfully separated and characterized. As a result, a new reaction route for ynone species is demonstrated, which is totally different from the existing allenamine activation model.

Graphical abstract: Highly efficient synthesis of benzodioxins with a 2-site quaternary carbon structure by secondary amine-catalyzed dual Michael cascade reactions

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Publication details

The article was received on 02 May 2018, accepted on 09 Jul 2018 and first published on 10 Jul 2018


Article type: Paper
DOI: 10.1039/C8OB01029C
Citation: Org. Biomol. Chem., 2018,16, 5533-5538
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    Highly efficient synthesis of benzodioxins with a 2-site quaternary carbon structure by secondary amine-catalyzed dual Michael cascade reactions

    X. He, Y. Li, M. Wang, H. Chen, B. Chen, H. Liang, Y. Zhang, J. Pang and L. Qiu, Org. Biomol. Chem., 2018, 16, 5533
    DOI: 10.1039/C8OB01029C

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