Palladium-catalyzed enantioselective synthesis of cyclohexene derivatives via kinetic resolution

✍ Scribed by Toyoki Nishimata; Kentaro Yamaguchi; Miwako Mori

• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 225 KB
• Volume: 40
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(99)01079-5

✦ Synopsis

Abltract: Reaction of (±)-methyl 2-arylcyclohexenyl carbonate with tosyl amide in the presence of a catalytic amount ot Pd.,dba.CHCl 3 and (S)-BINAPO produced 2-aryleyciohexenyl tosyl amide with a high ee along with the starting material with a high ee. The reaction involved two processes, and (+)-and (-)-methyl 2-arylcyclohexenyl carbonate gave the same (nallyl)palladium complex with a ehiral ligand, which gave 2-arylcyelohexenyl tosyl amide with a high ee by enantioselective substitution. The intermediary (~-allyi)palladium complex was synthesized, and the results of X-ray crystallography are shown.