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

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, thus, a versatile method for the preparation of chiral amines from the corresponding chiral alcohols is established.