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Organocatalytic atropo- and E/Z-selective Michael addition reaction of ynones with α-amido sulfones as sulfone-type nucleophile

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Abstract

We describe herein the first enantioselective organocatalytic Michael addition reaction of α-amido sulfones to ynones to access axially chiral styrenes. Sulfone-containing axially chiral styrene compounds were constructed with excellent enantioselectivity and almost complete E/Z-selectivity (up to 97% ee, >20 : 1 E/Z) in the presence of an easily accessible cinchona-alkaloid-derived multiple hydrogen-bonding catalyst. The enantioenriched sulfone-containing products were used as precursors for further transformations without any loss of the ee value. The equilibration process of this transformation was monitored by 1H NMR spectroscopy.

Graphical abstract: Organocatalytic atropo- and E/Z-selective Michael addition reaction of ynones with α-amido sulfones as sulfone-type nucleophile

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Publication details

The article was received on 14 Nov 2018, accepted on 16 Dec 2018 and first published on 18 Dec 2018


Article type: Research Article
DOI: 10.1039/C8QO01241E
Citation: Org. Chem. Front., 2019, Advance Article
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    Organocatalytic atropo- and E/Z-selective Michael addition reaction of ynones with α-amido sulfones as sulfone-type nucleophile

    N. Zhang, T. He, Y. Liu, S. Li, Y. Tan, L. Peng, D. Li, C. Shan and H. Yan, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C8QO01241E

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