Mitsunobu reaction

What is Mitsunobu reaction?

Mitsunobu reaction is an organic chemical reaction in which an alcohol is converted into an ester or a substituted alkene through the action of a reagent that can provide a leaving group, such as a phosgene, and a base, such as triphenylphosphine. The reaction was discovered by the Japanese chemist Yoshiaki Mitsunobu in the 1970s and is named after him..

Mitsunobu reaction
Mitsunobu reaction

Mitsunobu reaction typically proceeds through an intermediate called a “tosylate ester,” which is a compound that is formed when the alcohol reacts with the reagent and the base. The intermediate can then be hydrolyzed to produce the final ester product, or it can be reacted with another compound to produce a substituted alkene..

One of the key features of the Mitsunobu reaction is that it allows for the synthesis of esters and substituted alkenes from alcohols, which can be useful for synthesizing a wide range of compounds for various applications. Esters and substituted alkenes are also important intermediates in a number of chemical reactions and can serve as starting materials for the synthesis of other compounds..

Mitsunobu reaction can be performed under a variety of conditions, including both acidic and basic conditions. The choice of conditions depends on the specific reactants and desired product, and can be influenced by factors such as the stability of the intermediate and the ability to control the regiochemistry of the reaction..

Summary

Mitsunobu reaction is a useful tool for synthesizing esters and substituted alkenes and has a wide range of applications in the field of organic chemistry..

References

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