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- Title
Exploring the Metal-Catalyzed Reactions of α-Diazo-β-hydroxyamino Esters: Conversion of Cyclic Aldonitrones into Ketonitrones.
- Authors
Lieou Kui, Evelyn; Kanazawa, Alice; Philouze, Christian; Poisson, Jean‐François; Py, Sandrine
- Abstract
α-Diazo β-hydroxyamino esters, readily obtained by the addition of lithiated ethyl diazoacetate to cyclic nitrones, react smoothly in the presence of metal catalysts to produce ketonitrones. This transformation results from a selective 1,2-hydride shift of the metal carbenoid intermediates. The process is particularly efficient for diazo-N-hydroxypyrrolidine systems. For diazo-N-hydroxypiperidine substrates, C-H insertion can be a competitive reaction.
- Subjects
DIAZO compounds; METAL catalysts; HYDROXY esters; NITRONE derivatives; ALDO-keto reductases
- Publication
European Journal of Organic Chemistry, 2017, Vol 2017, Issue 2, p363
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201601255