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
Revue
European J. Org. Chem.
Volume
2017
Pagination
363–372
ISSN
1099-0690
Soumis le 12 avril 2018