Silver-Catalyzed 1,3-Dipolar Cycloaddition of Azomethine Ylides with β-Boryl Acrylates.
- Resource Type
- Article
- Authors
- López-Pérez, Ana; Segler, Marwin; Adrio, Javier; Carretero, Juan C.
- Source
- Journal of Organic Chemistry. 3/18/2011, Vol. 76 Issue 6, p1945-1948. 4p.
- Subject
- *RING formation (Chemistry)
*YLIDES
*ACRYLATES
*BORANES
*CATALYSTS
*PINACOL rearrangement
- Language
- ISSN
- 0022-3263
The Ag-catalyzed 1,3-dipolar cycloaddition of (?)-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. [ABSTRACT FROM AUTHOR]