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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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Abstract

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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Article information


Submitted
18 Sep 2012
Accepted
25 Oct 2012
First published
26 Oct 2012

Chem. Commun., 2012,48, 11978-11980
Article type
Communication

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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