• Citer

Préparation et attribution de configuration des cis-6-t-butyl-trans,cis- et trans,trans-2-décalols et des cis-6-t-butyl-cis,cis- et cis, trans-2-décalols. Equilibration des alcools épimeres

par Maes, M;Ottinger, Robert ;Reisse, Jacques ;Chiurdoglu, Grégoire
Référence Tetrahedron, 25, 21, page (5163-5175)
Publication Publié, 1969

Article révisé par les pairs

• Accès en ligne
• Détails
• Contenu
• Statistiques

Résumé :

The synthesis of cis-6-t-butyl-cis,cis-2-decalol, cis-6-t-butyl-cis,trans- 2-decalol, cis-6-t-butyl-trans,cis-2-decalol and cis-6-t-butyl-trans,trans-2-decalol has been achieved. The condensation of 4-t-butyl-1-morpholinocyclohex-1-ene with methylvinylketone gives cis-6-t-butyl-Δ1,9-2-octalone. By specific reduction of the ethylenic bond, it is easy to obtain cis-6-t-butyl-cis-2-decalone and cis-6-t-butyl-trans-2-decalone. These ketones were reduced under various conditions to give the corresponding alcohols. By means of RMN spectra and the thermodynamic data concerning the axial-equatorial equilibrium between the two systems of epimers, the configurations were determined. © 1969.