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Issue 36, 2015
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Stereocontrolled synthesis of vicinally functionalized piperidines by nucleophilic β-addition of alkyllithiums to α-aryl substituted piperidine enecarbamates

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Abstract

Substituted piperidines are emerging as important medicinally-active structural motifs. Here, we report highly stereoselective carbolithiation reactions of α-aryl piperidine enecarbamates that offer direct access to vicinally-substituted piperidine compounds. We have also demonstrated that the carbanion intermediates can be trapped with a carbon electrophile.

Graphical abstract: Stereocontrolled synthesis of vicinally functionalized piperidines by nucleophilic β-addition of alkyllithiums to α-aryl substituted piperidine enecarbamates

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The article was received on 11 Feb 2015, accepted on 26 Mar 2015 and first published on 26 Mar 2015


Article type: Communication
DOI: 10.1039/C5CC01307K
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Citation: Chem. Commun., 2015,51, 7653-7656
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    Stereocontrolled synthesis of vicinally functionalized piperidines by nucleophilic β-addition of alkyllithiums to α-aryl substituted piperidine enecarbamates

    T. K. Beng, H. Takeuchi, M. Weber and R. Sarpong, Chem. Commun., 2015, 51, 7653
    DOI: 10.1039/C5CC01307K

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