Iron(III)/Copper(II)-Cocatalyzed Cycloaddition/[3,3]-Rearrangement/N-O Bond Cleavage To Prepare Polysubstituted Pyrrolizines from N-Vinyl-α,ß-Unsaturated Nitrones and Activated Alkynes.
Org Lett
; 21(2): 481-485, 2019 01 18.
Article
en En
| MEDLINE
| ID: mdl-30628783
ABSTRACT
An efficient one-pot synthesis of polysubstituted pyrrolizines from N-vinyl- α,ß-unsaturated nitrones and activated alkynes through iron(III)/copper(II)-cocatalyzed [3 + 2] cycloaddition/[3,3]-rearrangement and sequential N-O bond cleavage was developed. The reaction first underwent [3 + 2] cycloaddition and [3,3]-rearrangement to afford nine-membered N-heterocycles, and then a controlled N-O bond cleavage of nine-membered rings by iron(III)/copper(II) cocatalysts delivered pyrrolizine scaffolds. A kinetic resolution of nine-membered ring compounds was achieved for the first time by using copper(II) acetate combined with a chiral PyBox ligand.
Texto completo:
1
Colección:
01-internacional
Base de datos:
MEDLINE
Idioma:
En
Revista:
Org Lett
Asunto de la revista:
BIOQUIMICA
Año:
2019
Tipo del documento:
Article
País de afiliación:
China