Organic letters

Lithiation and Reactions of Stilbene Oxides: Synthetic Utility

S Florio, V Aggarwal, A Salomone

Index: Florio, Saverio; Aggarwal, Varinder; Salomone, Antonio Organic Letters, 2004 , vol. 6, # 23 p. 4191 - 4194

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Citation Number: 32

Abstract

The lithiation of trans-and cis-stilbene oxides (±)-1 and 8 has been investigated. While with 8, lithiation occurred exclusively at the benzylic position, with the trans isomer (±)-1, ortho- lithiation competed with α-lithiation depending upon the experimental conditions. The configurational stability of the α-lithiated cis-and trans-stilbene oxides (±)-2 and (±)-9, respectively, was proved as well as that of scalemic stilbene oxide (R, R)-2.

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