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Mitsunobu reaction has several applications in the synthesis of natural products and pharmaceuticals.
The reaction mechanism of the Mitsunobu reaction is fairly complex.
The order of addition of the reagents of the Mitsunobu reaction can be important.
The Mitsunobu reaction has been applied in the synthesis of aryl ethers:
It is an epimer of codeine that can be prepared from it by a Mitsunobu reaction.
It has also been used as a reagent in the Mitsunobu reaction in place of diethyl azodicarboxylate.
Thioesters can be conveniently prepared from alcohols by the Mitsunobu reaction, using thioacetic acid.
Sharpless asymmetric epoxidation and Mitsunobu reaction have been used to produce expected (S)-dapoxetine.
He also developed the use of p-nitrobenzoate as a nucleophile for the displacement of activated alcohols in the Mitsunobu reaction.
It is often used in the Mitsunobu reaction where it serves as an oxidizer of triphenylphosphine to triphenylphosphine oxide.
Another method for the dehydration of mixtures of alcohols and carboxylic acids is the Mitsunobu reaction:
The other method involves the ring-opening reaction of an epoxide with amines, followed by ring closing with the Mitsunobu reaction.
Aliphatic alcohols give azides via a variant of the Mitsunobu reaction, with the use of hydrazoic acid.
A second Mitsunobu reaction then forms the aziridine 14 available for ring-opening reaction with 3-pentanol catalyzed by boron trifluoride to ether 15.
This hydroxyl group has the wrong stereochemistry and is therefore inverted in a Mitsunobu reaction with p-nitrobenzoic acid followed by hydrolysis of the p-nitrobenzoate to 13.
Stereochemical transformations (such as the Claisen rearrangement and Mitsunobu reaction) can remove or transfer the desired chirality thus simplifying the target.
PhPO is a by-product of many useful reactions in organic synthesis including the Wittig, Staudinger, and Mitsunobu reactions.
Phosphines are reducing agents, as illustrated in the Staudinger reduction converting azides to amines and in the Mitsunobu reaction for converting alcohols into esters.
Synthetically, α-naloxol can be prepared from naloxone by reduction of the ketone group, and β-naloxol can be prepared from α-naloxol by a Mitsunobu reaction.
The hydroxyl group is replaced in a Mitsunobu reaction by an azide group with diphenylphosphoryl azide in 7 and acid hydrolysis yields the azido aldehyde 8.
Hydrogenation with Raney nickel gives the diol 9 which on a double Mitsunobu reaction (with an amine proton donor) gives the azafenestrane 10 as the borane salt.
The next step converting the alcohol group to an amine in 60 was a Mitsunobu reaction (hydrogen azide, DEAD, triphenylphosphine with azide reduction to amine by PhP).
DEAD is an important reagent in the Mitsunobu reaction where it forms an adduct with phosphines (usually triphenylphosphine) and assists the synthesis of esters, ethers, amines and thioethers of alcohols.
The remainder of the carbon framework is added with chiral propargyl alcohol 3 (introducing the 4a stereocenter and obtained by chiral synthesis of the ketone with R-Alpine borane) in a Mitsunobu reaction to aryl ether 4.
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).