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C6′ steric bulk of cinchona alkaloid enables an enantioselective Michael addition/annulation sequence toward pyranopyrazoles

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Abstract

A catalytic asymmetric Michael addition/annulation process between pyrazolones and enynones towards enantioenriched pyranopyrazoles was developed. Key features include the development of a cinchona alkaloid with C6′ steric bulk as a competent catalyst and the observation of a unique stereospecific deuteration α to the keto group via a conducted tour pathway.

Graphical abstract: C6′ steric bulk of cinchona alkaloid enables an enantioselective Michael addition/annulation sequence toward pyranopyrazoles

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Publication details

The article was received on 08 Jan 2018, accepted on 29 Jan 2018 and first published on 29 Jan 2018


Article type: Communication
DOI: 10.1039/C8CC00154E
Citation: Chem. Commun., 2018, Advance Article
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    C6′ steric bulk of cinchona alkaloid enables an enantioselective Michael addition/annulation sequence toward pyranopyrazoles

    X. Bao, S. Wei, J. Qu and B. Wang, Chem. Commun., 2018, Advance Article , DOI: 10.1039/C8CC00154E

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