Asymmetric Allylic Oxidation with Biarylbisoxazoline-Copper(I) Catalysis

✍ Scribed by Merritt B Andrus; Davoud Asgari

• Book ID: 104202786
• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 126 KB
• Volume: 56
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(00)00425-7

✦ Synopsis

AbstractÐEight new bi-o-tolyl bisoxazolines were made and used as ligands in the copper catalyzed asymmetric allylic oxidation reaction. Three benzoyl tert-butyl peresters, p-nitro, o-iodo, and 2,4,6-trichloro were made and used with cyclohexene and cyclopentene with the ligands complexed to copper(I) hexa¯uorophosphate (10 mol%). High selectivities (73% ee, 78% yield) were obtained with the nitroperester and 1a (S,S,S RPh) and cyclohexene. For the cyclopentene, 1c (RBn) was best at 72% ee, 63% yield.