An Explanation of a-Cyanocinnamate Esters as a Replacement for DEAD in the Mitsunobu Reaction

Abstract

The Mistunobu reaction was first reported by Oyo Mitsunobu in the Bulletin of the Chemical Society of Japanin 1967, with a follow-up review in Synthesisin 1981. A recent literature search using Web of Science reveals that between them, these two papers have amassed over 5,000 citations. The reaction proceeds by coupling the desired SN2 substitution with an exothermic redox reaction and dehydration. The formation of the phosphoryl (P=O) group provides much of the driving force for the reaction.