Terpenyl tellurides—Synthesis and application in asymmetric epoxidation

GRAPHICAL ABSTRACT

ABSTRACT

This work presents a synthesis of new group of unsymmetrical chiral tellurides obtained in the reaction of sodium methanetellurolate or sodium benzenetellurolate with appropriate terpenyl tosylates from p-menthane, carane, and pinane systems. Additionally, symmetrical diterpenyl tellurides were prepared according to our recently published method using sodium telluride and terpenyl tosylates. Methyl terpenyl, phenyl terpenyl, and diterpenyl tellurides were successfully used in tellurium ylide-mediated asymmetric epoxidation reaction. The best result of asymmetric epoxidation was obtained for dicaranyl telluride (d.r. cis:trans 11:89, e.r. trans 84:16).

KEYWORDS:

• Tellurides
• terpenes
• asymmetric epoxidation