Stereoselective synthesis of optically active phenyl ethers

Reacting the 1,2-naphthalenedisulfonimide of (S)-α-methylbenzylamine with phenol gave the corresponding α-methylbenzyl phenyl ether with 46% e.e. Synthesis of the authentic optically active phenyl ethers was accomplished under mild, neutral conditions by generating benzyne in the presence of optically active (R)-α-methylbenzyl alcohol. Benzyne was generated by reacting anthranilic acid with tert-butyl nitrite in refluxing monoglyme.