Enantiomerically pure trifluoromethyl derivatives of terpenoids

A convenient and simple method has been found for the preparation of trifluoromethylated monoterpenes and their derivatives such as cyclopentanoids which could serve as synthetic intermediates, mechanistic and 19F NMR probes. The method involves, in general, treatment of carboxylic derivatives of terpenes, particularly camphor, with sulfur tetrafluoride under mild conditions. The fluorination proceeds with full retention of configuration at all chiral carbon atoms affording enantiopure trifluoromethyl derivatives.