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Issue 98, 2012
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Synthesis and asymmetric hydrogenation of (3E)-1-benzyl-3-[(2-oxopyridin-1(2H)-yl)methylidene]piperidine-2,6-dione

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The synthesis of (3E)-1-benzyl-3-[(2-oxopyridin-1(2H)-yl)methylidene]piperidine-2,6-dione 4 from N-benzylglutarimide was achieved in three steps. The asymmetric hydrogenation of 4 gave either the product of partial reduction (10) or full reduction (13), depending on the catalyst which was employed, in high ee in each case. Attempts at asymmetric transfer hydrogenation (ATH) of 4 resulted in formation of a racemic product.

Graphical abstract: Synthesis and asymmetric hydrogenation of (3E)-1-benzyl-3-[(2-oxopyridin-1(2H)-yl)methylidene]piperidine-2,6-dione

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The article was received on 18 Sep 2012, accepted on 25 Oct 2012 and first published on 26 Oct 2012

Article type: Communication
DOI: 10.1039/C2CC36807B
Citation: Chem. Commun., 2012,48, 11978-11980
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    Synthesis and asymmetric hydrogenation of (3E)-1-benzyl-3-[(2-oxopyridin-1(2H)-yl)methylidene]piperidine-2,6-dione

    A. A. Bisset, A. Shiibashi, J. L. Desmond, A. Dishington, T. Jones, G. J. Clarkson, T. Ikariya and M. Wills, Chem. Commun., 2012, 48, 11978
    DOI: 10.1039/C2CC36807B

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