Exploring the Metal-Catalyzed Reactions of α-Diazo-β-hydroxyamino Esters: Conversion of Cyclic Aldonitrones into Ketonitrones.
α-Diazo β-hydroxyamino esters, readily obtained by the addn. of lithiated Et 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. [on SciFinder(R)]
Références
- Titre
- Exploring the Metal-Catalyzed Reactions of α-Diazo-β-hydroxyamino Esters: Conversion of Cyclic Aldonitrones into Ketonitrones.
- Type de publication
- Article de revue
- Année de publication
- 2017
- Auteurs
- Lieou-Kui, Evelyn, Kanazawa Alice, Philouze Christian, Poisson Jean-François, and Py Sandrine
- Revue
- European J. Org. Chem.
- Volume
- 2017
- Pagination
- 363–372
- ISSN
- 1099-0690
Soumis le 12 avril 2018