C(1)-Substituted menthol derivatives: Self-removing chiral auxiliaries for asymmetric conjugate additions to cycloalkenones

✍ Scribed by Raymond L. Funk; Ge Yang

• Book ID: 104260581
• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 137 KB
• Volume: 40
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(98)02627-6

✦ Synopsis

C(l)-substituted (-)-menthone derivatives 3 were prepared by the stereoselective addition of the alkenyllithium reagents 9 to menthone (8) and subsequent acid catalyzed hydrolysis of the dioxolane protecting groups. Conjugate addition of cuprate reagents to enones 3a,b followed by a methanol quench directly gave the [~-alkylcycloalkanones 7 via retro-aldol reactions in 80-91% ee.