New zinc(II)-based catalyst for asymmetric azomethine ylide cycloaddition reactions.
[reaction: see text] A new chiral aziridino alcohol ligand for zinc(II)-catalyzed azomethine ylide cycloadditions is described. In the presence of this catalyst, N-arylidene glycine methyl esters react with a variety of dipolarophiles to give substituted pyrrolidines in very good to excellent chemical yields and up to 95% ee. The absolute sense of asymmetric induction appears to be dipolarophile-dependent.
Dogan
Ozdemir
O
Department of Chemistry, Middle East Technical University, 06531 Ankara, Turkey. dogano@metu.edu.tr
Koyuncu
Hasan
H
Garner
Philip
P
Bulut
Adnan
A
Youngs
Wiley J
WJ
Panzner
Matthew
M
D001388:Aziridines / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D005998:Glycine / Q000031:analogs & derivatives* / Q000737:chemistry; D008024:Ligands; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D015032:Zinc / Q000737:chemistry*
D001388:Aziridines; D008024:Ligands; D011759:Pyrrolidines; C035591:glycine methyl ester; D015032:Zinc; D005998:Glycine