Stereoselective access to hydroxy oxetanes and tetrahydrooxepines through isomerization of oxiranyl ethers

A Mordini, S Bindi, A Capperucci, D Nistri…

Index: Mordini; Bindi; Capperucci; Nistri; Reginato; Valacchi Journal of Organic Chemistry, 2001 , vol. 66, # 9 p. 3201 - 3205

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Citation Number: 25

Abstract

We have shown in the past few years1-3 that allyl, benzyl, and propargyl 2, 3-epoxy ethers (1a, 1b, and 1c, respectively, Scheme 1) can be regio-and stereoselectively converted into 2- vinyl-, 2-phenyl-, or 2-alkynyl-3-(R-hydroxyalkyl) oxetanes (2a, 2b, and 2c, respectively) by treatment with the Schlosser's base4 (butyllithium/potassium tert-butoxide) or other superbasic mixtures5, 6 such as lithium diisopropylamide/potassium tert-butoxide ( ...

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