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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). [ABSTRACT FROM PUBLISHER]

Convenient routes for the synthesis of optically active methyl, phenyl, and dimonoterpenyl sulfides derived from carane,p-menthane, pinane, and bornane were developed. Methyl and dimonoterpenyl sulfides have been obtained by the reaction of the corresponding monoterpene thiolates with methyl iodide or monoterpene tosylates. The reactions of monoterpene tosylates with sodium benzenethiolate gave the corresponding phenyl monoterpenyl sulfides. These sulfides were used for the sulfur ylide-mediated reaction to yield epoxides. Good diastereoselectivities up to 99:1 and low to moderate enantioselectivities were observed for the enantioselective synthesis of chiral epoxides. [ABSTRACT FROM PUBLISHER]