CATALYTIC OXIDATIVE CLEAVAGE OF TERPENIC OLEFINS: USEFUL ROUTE TO CHIRAL POLY-FUNCTIONALISED CYCLOBUTANES AND CYCLOPROPANES

Hosni Ziyat, Mustapha Ait Ali,* Abdalah Karim, Catherine Meliet, Yves Castanet, and Andre Mortreux

Laboratoire de Chimie de Coordination, Faculté des Sciences-Semlalia BP 2390 Marrakech (Morocco),

E-mail: aitali@ucam.ac.ma

Laboratoire de Catalyse de Lille, Groupe de Chimie Organique Appliqué, UPRESA 8010, ENSC Lille,

BP 108, 59642 Villeneuve d’Ascq (France)

Abstract

Catalytic oxidation of terpenic olefins (a-pinene, 2-carene and 3-carene) with RuO₄ generated in situ, produces the cyclobutane and cyclopropane isolable keto-aldehydes which evolve in prolonged reaction time to the corresponding keto-acids with excellent yields (90-100%). As these compounds can serve as building block for the synthesis of cyclobutane aminoacids and pyrethroid derivatives, the reaction affords a simple access to this class of compounds.

Key words: ruthenium, oxidation, cleavage, terpenes