Silver-Catalyzed 1,3-Dipolar Cycloaddition of Azomethine Ylides with β-Boryl Acrylates

The Ag-catalyzed 1,3-dipolar cycloaddition of (Ε)-β-borylacrylates with azomethine ylides is described. The resulting 3-borylpyrrolidine derivatives were obtained in high yields and complete endo selectivities using AgOAc/dppe as catalyst system and B(dam) as boryl group. Transformation of the B(dam...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Journal of organic chemistry 2011-03, Vol.76 (6), p.1945-1948
Hauptverfasser:	López-Pérez, Ana, Segler, Marwin, Adrio, Javier, Carretero, Juan C
Format:	Artikel
Sprache:	eng
Schlagworte:	Acrylates - chemistry Azo Compounds - chemistry Catalysis Catalysts: preparations and properties Chemistry Exact sciences and technology General and physical chemistry Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Organic chemistry Preparations and properties Silver - chemistry Stereoisomerism Substrate Specificity Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry Thiosemicarbazones - chemistry
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

Beschreibung
Zusammenfassung:	The Ag-catalyzed 1,3-dipolar cycloaddition of (Ε)-β-borylacrylates with azomethine ylides is described. The resulting 3-borylpyrrolidine derivatives were obtained in high yields and complete endo selectivities using AgOAc/dppe as catalyst system and B(dam) as boryl group. Transformation of the B(dam) group into pinacol borane and oxidation afforded 3-hydroxyproline derivatives in high yields.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo1024915