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

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

The synthesis of (3E)-1-benzyl-3-[(2-oxopyridin-1(2H)-yl)methylidene]piperidine-2,6-dione 5 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,...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) Vol. 48; no. 98; p. 11978
Main Authors: Bisset, Alexander A, Shiibashi, Akira, Desmond, Jasmine L, Dishington, Allan, Jones, Teyrnon, Clarkson, Guy J, Ikariya, Takao, Wills, Martin
Format: Journal Article
Language:English
Published: England 01-01-2012
Subjects:
Benzyl Compounds - chemical synthesis
Benzyl Compounds - chemistry
Hydrogenation
Molecular Structure
Piperidones - chemical synthesis
Piperidones - chemistry
Stereoisomerism
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Summary:The synthesis of (3E)-1-benzyl-3-[(2-oxopyridin-1(2H)-yl)methylidene]piperidine-2,6-dione 5 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 resulted in formation of a racemic product.
ISSN:1364-548X
DOI:10.1039/c2cc36807b