Tetrahedron

Conversion of tertiary alcohols to tert-alkyl azides by way of quinone-mediated oxidation–reduction condensation using alkyl diphenylphosphinites

K Kuroda, Y Hayashi, T Mukaiyama

Index: Kuroda, Kiichi; Hayashi, Yujiro; Mukaiyama, Teruaki Tetrahedron, 2007 , vol. 63, # 27 p. 6358 - 6364

Full Text: HTML

Citation Number: 12

Abstract

A novel method for the preparation of alkyl azides from alcohols by way of oxidation– reduction condensation is described. In this reaction, the sterically-hindered tert-alkyl phosphinites that are prepared from the corresponding alcohols are converted into tert-alkyl azides with almost complete inversion of their stereochemistry: the obtained alkyl azides are then successfully reduced to afford the corresponding amines on treatment with LiAlH4, ...