The first enantioselective intramolecular aminocarbonylation of alkenes promoted by Pd(II)-spiro bis(isoxazoline) catalyst

✍ Scribed by Toshio Shinohara; Midori A. Arai; Kazuhiko Wakita; Takayoshi Arai; Hiroaki Sasai

• Book ID: 104252743
• Publisher: Elsevier Science
• Year: 2003
• Tongue: French
• Weight: 116 KB
• Volume: 44
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(02)02650-3

✦ Synopsis

The highly ligand acceleration effect of spiro bis(isoxazoline) ligand (SPRIX) on the Pd(II)-catalyzed intramolecular aminocarbonylation of alkenyl amine derivatives was realized. Furthermore, the chiral Pd(II)-SPRIX catalyst accomplished the first enantioselective intramolecular aminocarbonylation. The reaction of N-(2,2-dimethyl-pent-4-enyl)-p-toluenesulfonamide in the presence of Pd(II)-SPRIX catalyst and p-benzoquinone in methanol under a carbon monoxide atmosphere afforded [4,4-dimethyl-1-(p-toluene-sulfonyl)-pyrrolidin-2-yl]-acetic acid methyl ester in good yield with moderate enantioselectivity.