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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Published in:Chemical communications (Cambridge, England) England), 2012-01, Vol.48 (98), p.11978-11980
Main Authors: Bisset, Alexander A, Shiibashi, Akira, Desmond, Jasmine L, Dishington, Allan, Jones, Teyrnon, Clarkson, Guy J, Ikariya, Takao, Wills, Martin
Format: Article
Language:English
Subjects:
Benzyl Compounds - chemical synthesis
Benzyl Compounds - chemistry
Hydrogenation
Molecular Structure
Piperidones - chemical synthesis
Piperidones - chemistry
Stereoisomerism
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description 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.
doi_str_mv 10.1039/c2cc36807b
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source Royal Society of Chemistry:Jisc Collections:Royal Society of Chemistry Read and Publish 2022-2024 (reading list)
subjects Benzyl Compounds - chemical synthesis
Benzyl Compounds - chemistry
Hydrogenation
Molecular Structure
Piperidones - chemical synthesis
Piperidones - chemistry
Stereoisomerism
title Synthesis and asymmetric hydrogenation of (3E)-1-benzyl-3-[(2-oxopyridin-1(2H)-yl)methylidene]piperidine-2,6-dione
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