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Communication | Special issue | Vol 39, No. 1, 1994, pp.59-66
Published online, 1st January, 1970
DOI: 10.3987/COM-94-S(B)42
General Stereoselective Route to (E)-3-Hydroxy-1-alkenyl Chlorides and Phenyl Ethers

Seiichi Takano,* Yoshiaki Sugihara, and Kunio Ogasawara

*Pharnaceutical Institute, Tohoku University, Aramaki, Aoba-ku, sendai 980-8578, Japan


Treatment of 2,3-epoxyalkyl chlorides with potassium tert-butoxide affords the corresponding (E)-1-chloro-3-hydroxyalkenes stereoselectively when dicyclohexano-18-crown-6 is present. On the other hand, 2,3-epoxyalkyl phenyl ethers furnish (E)-3-hydroxy-1-alkenyl phenyl ethers stereoselectively upon exposure to n-butyllithium in the presence of hexamethylphosphoric triamide.