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Highly Efficient Synthesis of Benzodioxins with a 2-Site Quaternary Carbon Structure by Secondary Amine-Catalyzed Dual Michael Cascade Reactions

Abstract

Salicylic acids and substituted ynones were employed as the 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 was successfully separated and charactirized in the cascade process. As a result, a new reaction route for ynone species was demonstrated, which was totally different from the existing allenamine activation model.

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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, Accepted Manuscript
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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, Accepted Manuscript , DOI: 10.1039/C8OB01029C

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