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Issue 40, 2017
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Enantioselective organocatalytic Michael additions of N,N′-dialkylbarbituric acids to enones

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Abstract

N,N′-Dialkylbarbituric acids as cyclic malonamide donors were successfully used in the enantioselective Michael addition reaction of enones. Using cinchona alkaloid-based bifunctional squaramide as an organocatalyst, this Michael reaction of N,N′-di-tert-butylbarbituric acid with various enones features a highly enantioselective (91–99% ee) production of the corresponding optically active 5-substituted barbituric acid derivatives. The transformations of the Michael product for the barbituric acid structural unit were realized in two ways, deprotection to remove the N-tert-butyl group and alkylation to produce 5,5-disubstituted barbituric acid derivatives.

Graphical abstract: Enantioselective organocatalytic Michael additions of N,N′-dialkylbarbituric acids to enones

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Publication details

The article was received on 24 Aug 2017, accepted on 27 Sep 2017 and first published on 27 Sep 2017


Article type: Paper
DOI: 10.1039/C7OB02116J
Citation: Org. Biomol. Chem., 2017,15, 8669-8679
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    Enantioselective organocatalytic Michael additions of N,N′-dialkylbarbituric acids to enones

    Y. Liu, Y. Zhang, H. Duan, D. Wanyan and Y. Wang, Org. Biomol. Chem., 2017, 15, 8669
    DOI: 10.1039/C7OB02116J

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