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s P O PhO PhO Cl NaN3 (1.2 equiv), acetone P O PhO PhO N3 reduced-pressure distillation 96% (A) Yamada and co-workers developed an improved method for the Curtius rearrangement reaction using DPPA, which was later named Yamada–Curtius rearrangement.1 In 2007, the Ciufolini group employed this method in the total synthesis of streptonigrone, to transform a carboxylic acid group into a protected amino group through the hydrolysis of an isocyanate intermediate.10 (B) A primary or secondary alcohol can be easily converted into an azide group by DPPA under mildly basic conditions or using Mitsunobu conditions for stereochemical inversion. In the total synthesis of cribrostatin VI, the Danishefsky group successfully employed DPPA to displace a benzyl alcohol in high yield and ee.11 Another example was demonstrated in the synthesis of Tamiflu and its phosphonate congeners by the Wang group in 2007.12 N N OMe

Diphenylphosphoryl Azide (DPPA) - A Reagent with Manifold Applications