Reaction of trifluoromethyl ketones. IV. Cyclization of the ene reaction products of trifluoromethyl ketones: A facile synthesis of 2-(trifluoromethyl)tetrahydrofuran.

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Abstract
1- (Trifluoromethyl) homoallyl alcohols, which were obtained by the ene reaction of trifluoromethyl ketones with olefins, were cyclized to 2-(trifluoromethyl) tetrahydrofurans in the presence of p-toluenesulfonic acid, a typical Brensted acid. The ease of this cyclization depends on the substituents on the homoallyl system. The stereochemistry of the cyclization products was established by analysis of the two dimensional nuclear Overhauser effects. The stable conformations of the tetrahydrofuran compounds were estimated by means of molecular mechanics calculations of the steric energy. The observed ratio of the products was consistent with that estimated from the steric energy calculations.

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