Cu-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides with beta-phenylsulfonyl enones. Ligand controlled diastereoselectivity reversal.
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.
Robles-Machín
Rocío
R
Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain.
González-Esguevillas
María
M
Adrio
Javier
J
Carretero
Juan C
JC
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*
D001391:Azo Compounds; D008024:Ligands; D013450:Sulfones; D013882:Thiosemicarbazones; C512188:azomethine; D003300:Copper