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Issue 23, 2012
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Enantioselective trapping of an α-chiral carbanion of acyclic nitrile by a carbon electrophile

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Abstract

An α-chiral nitrile carbanion generated by deprotonation of enantioenriched O-carbamoyl cyanohydrin was trapped in situ with ethyl cyanoformate to give the corresponding ester derivative in 92% yield and 90 : 10 er, providing the first example of trapping of an α-chiral acyclic nitrile carbanion that has been considered to be very configurationally labile.

Graphical abstract: Enantioselective trapping of an α-chiral carbanion of acyclic nitrile by a carbon electrophile

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Publication details

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


Article type: Communication
DOI: 10.1039/C2CC00082B
Citation: Chem. Commun., 2012,48, 2897-2899

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    Enantioselective trapping of an α-chiral carbanion of acyclic nitrile by a carbon electrophile

    M. Sasaki, T. Takegawa, H. Ikemoto, M. Kawahata, K. Yamaguchi and K. Takeda, Chem. Commun., 2012, 48, 2897
    DOI: 10.1039/C2CC00082B

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