Nitrogen compounds Mitsunobu reaction

Once again, there has been considerable activity relating to the Mitsunobu and Staudinger reactions, in which nucleophilic attack by phosphorus at nitrogen is the initial step. The mechanistic complexity of the Mitsunobu reaction is confirmed following a further study of the various intermediates arising from the interaction of dialkyl azodicarboxylates with P(iii) compounds. Efforts have continued to effect improvements in S5mthetic applications of the Mitsunobu reaction, the main... 

Mitsunobu conditions are effective for glycosylation of weak nitrogen nucleophiles, such as indoles. This reaction has been used in the synthesis of antitumor compounds. 

The reaction of -protected aminomalonate with the Mitsunobu reagent (TPP and DIAD) gave a mixture of a triazoline as the main product and 53 (31%). This compound was formed by the attack of the azodicarboxylate oxygen rather than nitrogen during the cyclization step (88TL4661). 

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