Intramolecular palladium catalyzed alkoxy carbonylation of 6-hydroxy-1-octenes. Stereoselective synthesis of substituted tetrahydropyrans

✍ Scribed by James D. White; Jian Hong; Lonnie A. Robarge

• Book ID: 104260630
• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 184 KB
• Volume: 40
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(98)02693-8

✦ Synopsis

The reaction of hydroxy alkenes 5, 7, and 8 with CO and MeOH in the presence of PdCI 2 and CuCI 2 gave tetrahydropyrans 9, 11, and 12, respectively. Yields were dependent upon the configuration of substituents in the hydroxy alkene; in all cases, the tetrahydropyran was produced with 2,6-cis configuration.