title: Cu-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides with beta-phenylsulfonyl enones. Ligand controlled diastereoselectivity reversal.
abstract: A catalytic asymmetric procedure for the 1,3-dipolar cycloaddition of (E)-beta-phenylsulfonyl enones with azomethine ylides to provide highly functionalized pyrrolidine derivatives is described. In the presence of chiral Cu(I)-Segphos catalysts the adducts were obtained with high regio-, diastereo-, and enantioselectivity. Interestingly, a switch from endo to exo selectivity was observed when Segphos or DTBM-Segphos ligand was used.
authors: Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain.
authors: Rocío
authors: R
authors: Robles-Machín
authors: María
authors: M
authors: González-Esguevillas
authors: Javier
authors: J
authors: Adrio
authors: Juan C
authors: JC
authors: Carretero
mesh_terms: D001391:Azo Compounds / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D008024:Ligands; D015394:Molecular Structure; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry*; D013882:Thiosemicarbazones / Q000737:chemistry*
chemical_list: D001391:Azo Compounds; D008024:Ligands; D013450:Sulfones; D013882:Thiosemicarbazones; C512188:azomethine; D003300:Copper