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Issue 18, 2015
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Enantioselective synthesis of dihydrocoumarin derivatives by chiral scandium(III)-complex catalyzed inverse-electron-demand hetero-Diels–Alder reaction

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Abstract

An asymmetric inverse-electron-demand hetero-Diels–Alder reaction between o-quinone methides and azlactones to generate potentially pharmacological active dihydrocoumarins has been achieved efficiently by using a chiral N,N′-dioxide–Sc(III) complex as the catalyst. The desired products were obtained in high yields with excellent enantioselectivities and diastereoselectivities (up to 94% yield, 96% ee and >19 : 1 dr) under mild reaction conditions. A concerted reaction pathway was confirmed by Operando IR and control experiments.

Graphical abstract: Enantioselective synthesis of dihydrocoumarin derivatives by chiral scandium(iii)-complex catalyzed inverse-electron-demand hetero-Diels–Alder reaction

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Publication details

The article was received on 27 Dec 2014, accepted on 27 Jan 2015 and first published on 04 Feb 2015


Article type: Communication
DOI: 10.1039/C4CC10343B
Citation: Chem. Commun., 2015,51, 3835-3837
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    Enantioselective synthesis of dihydrocoumarin derivatives by chiral scandium(III)-complex catalyzed inverse-electron-demand hetero-Diels–Alder reaction

    H. Hu, Y. Liu, J. Guo, L. Lin, Y. Xu, X. Liu and X. Feng, Chem. Commun., 2015, 51, 3835
    DOI: 10.1039/C4CC10343B

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