Overall Score4
- Generality
- Reagent Availability
- Experimental User Friendliness
- Criteria #4
- Criteria #5
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General Characteristics
First introduced in 1970’s, 2-halo-N-alkylpyridinium salts are called the Mukaiyama reagent and used for condensation reactions such as esterification and amide bond formation.
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General References
・Narasaka, K.; Maruyama, K.; Mukaiyama, T. Chem. Lett. 1978, 885. doi:10.1246/cl.1978.885
・Review for macrolactonization: Parenty, A.; Moreau, X.; Campagne, J.-M. Chem. Rev. 2006, 106, 911. DOI: 10.1021/cr0301402
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Reaction Mechanism
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Examples
The synthesis of prostaglandin F-lactone.[1]
An application to macrolactamization.[2]
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Experimental Procedure
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Experimental Tips
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References
[1] Narasaka, K.; Maruyama, K.; Mukaiyama, T. Chem. Lett. 1978, 885. doi:10.1246/cl.1978.885
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Related Reactions
- Protection of Carboxylic Acid
- Condensation Reagent
- Keck Macrolactonization
- Fischer-Speier Esterification
- Acyl Protective Group
- Yamaguchi Macrolactonizaion
- Mukaiyama Redox Condensation
- Corey-Nicolaou Macrolactonizaion
- Mitsunobu Reaction
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Related Books
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External Links