Mitsunobu reaction

chemical reaction

The Mitsunobu reaction is an organic reaction that converts an alcohol into a variety of functional groups, such as an ester, using triphenylphosphine and an azodicarboxylate such as diethyl azodicarboxylate (DEAD) or diisopropyl azodicarboxylate (DIAD).

QuotesEdit

  • The availability of a stereodefined alcohol from reduction of a cyclic ketone raises the question of how one can obtain the corresponding stereoisomer.
    A solution to this problem is the Mitsunobu reaction, which provides a powerful tool for inverting the configuration of a given alcohol to its stereoisomer. The reaction involves conversion of the alcohol into a good leaving group capable of being displaced by a relatively weak nucleophile, generally a carboxylate ion (RCOO-). The product of stereochemical inversion is an ester, which on saponification leads to the alcohol of opposite configuration.
    • George S. Zweifel and Michael H. Nantz, Modern Organic Synthesis (2006), Ch. 4 : Functional Group Transformations: Oxidation and Reduction

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