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Issue 9, 2018
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Asymmetric [4+2] annulations to construct norcamphor scaffolds with 2-cyclopentenone via double amine–thiol catalysis

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Abstract

An efficient double catalytic system, combining chiral amine and 2-mercaptobenzoic acid, is applied for α′,β-regioselective [4+2] annulations of 2-cyclopentenone with a diversity of activated alkenes, constructing multifunctional chiral bicycle[2,2,1]heptane scaffolds in good to excellent yields and enantioselectivities. In comparison with the traditional cross-dienamine species between 2-cyclopentenone and chiral amine, the interrupted enamine intermediate containing a covalently linked thiol catalyst shows significantly improved reactivity.

Graphical abstract: Asymmetric [4+2] annulations to construct norcamphor scaffolds with 2-cyclopentenone via double amine–thiol catalysis

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Publication details

The article was received on 01 Dec 2017, accepted on 06 Jan 2018 and first published on 08 Jan 2018


Article type: Communication
DOI: 10.1039/C7CC09221K
Citation: Chem. Commun., 2018,54, 1129-1132
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    Asymmetric [4+2] annulations to construct norcamphor scaffolds with 2-cyclopentenone via double amine–thiol catalysis

    Q. Yang, W. Xiao, W. Du, Q. Ouyang and Y. Chen, Chem. Commun., 2018, 54, 1129
    DOI: 10.1039/C7CC09221K

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