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Issue 45, 2012
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Chiral proton catalysis of secondary nitroalkane additions to azomethine: synthesis of a potent GlyT1 inhibitor

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Abstract

The first enantioselective synthesis of a potent GlyT1 inhibitor is described. A 3-nitroazetidine donor is used in an enantioselective aza-Henry reaction catalyzed by a bis(amidine)-triflic acid salt organocatalyst, delivering the key intermediate with 92% ee. This adduct is reductively denitrated and converted to the target through a short sequence, thereby allowing assignment of the absolute configuration of the more potent enantiomer.

Graphical abstract: Chiral proton catalysis of secondary nitroalkane additions to azomethine: synthesis of a potent GlyT1 inhibitor

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Publication details

The article was received on 27 Mar 2012, accepted on 05 Apr 2012 and first published on 30 Apr 2012


Article type: Communication
DOI: 10.1039/C2CC32225K
Citation: Chem. Commun., 2012,48, 5578-5580
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    Chiral proton catalysis of secondary nitroalkane additions to azomethine: synthesis of a potent GlyT1 inhibitor

    T. A. Davis, M. W. Danneman and J. N. Johnston, Chem. Commun., 2012, 48, 5578
    DOI: 10.1039/C2CC32225K

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