Tetrahedron

Superbase-promoted rearrangement of oxiranes to cyclopropanes

A Mordini, D Peruzzi, F Russo, M Valacchi, G Reginato…

Index: Mordini, Alessandro; Peruzzi, Daniela; Russo, Francesco; Valacchi, Michela; Reginato, Gianna; Brandi, Alberto Tetrahedron, 2005 , vol. 61, # 13 p. 3349 - 3360

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Citation Number: 23

Abstract

Aryl-and alkenyl substituted oxiranes, when submitted to treatment with superbasic reagents, undergo a highly regio-and stereoselective rearrangement leading to cyclopropylmethanol derivatives. The process can also be applied to mono-and dihydroxy substituted substrates thus leading to polyhydroxylated cyclopropanes.

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