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Issue 1, 2014
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Chiral primary amine catalysed asymmetric conjugate addition of azoles to α-substituted vinyl ketones

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Abstract

We report here the first effective example of asymmetric conjugate addition–protonation reactions of azoles to vinyl ketones by chiral primary amine catalysis. High enantioselectivity can be easily achieved by screening different primary amine catalysts, and the Curtin–Hammett control in the C–N bond formation step was verified by DFT calculations to account for the observed stereoselectivity.

Graphical abstract: Chiral primary amine catalysed asymmetric conjugate addition of azoles to α-substituted vinyl ketones

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The article was received on 05 Nov 2013, accepted on 28 Nov 2013 and first published on 19 Dec 2013


Article type: Research Article
DOI: 10.1039/C3QO00027C
Citation: Org. Chem. Front., 2014,1, 68-72
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    Chiral primary amine catalysed asymmetric conjugate addition of azoles to α-substituted vinyl ketones

    N. Fu, L. Zhang, S. Luo and J. Cheng, Org. Chem. Front., 2014, 1, 68
    DOI: 10.1039/C3QO00027C

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