Steric effect in regioselective cyclization of 3, 4-epoxy alcohols to oxetanes.

T Masamune, S Sato, A Abiko, M Ono…

Index: Masamune, Tadashi; Sato, Shingo; Abiko, Atsushi; Ono, Mitsunori; Murai, Akio Bulletin of the Chemical Society of Japan, 1980 , vol. 53, # 10 p. 2895 - 2904

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Citation Number: 19

Abstract

A number of 3, 4-epoxy alcohols, involving critical structural factors for oxetane formation by intramolecular cyclization, were prepared and treated with base under aqueous (KOH in 75% aq DMSO) and anhydrous conditions (NaH in THF). The result of the reactions of cis- and trans-4, 5-epoxy-2-rnethyl-2-undecanols, coupled with that of 1-(2, 3-epoxybutyl)-and 1- (2, 3-epoxy-3-methylbutyl)-1-cyclohexanols (1a and 1b), indicated that the regioselective ...