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The Compatibility of Groups Used to Protect Phenolic Functionality during Oxone-Mediated Oxidative Esterification
Laboratory of Medicinal Chemistry, Faculty of Pharmacy, Takasaki University of Health and Welfare, Takasaki, Japan
Laboratory of Medicinal Chemistry, Faculty of Pharmacy, Takasaki University of Health and Welfare, Takasaki, Japan
Laboratory of Molecular Design Chemistry, Faculty of Pharmacy, Takasaki University of Health and Welfare, Takasaki, Japan
Laboratory of Medicinal Chemistry, Faculty of Pharmacy, Takasaki University of Health and Welfare, Takasaki, Japan
Laboratory of Organic Chemistry, Faculty of Pharmaceutical Sciences, Sojo University, Kumamoto, Japan
- 1 Laboratory of Medicinal Chemistry, Faculty of Pharmacy, Takasaki University of Health and Welfare, Takasaki, Japan
- 2 Laboratory of Medicinal Chemistry, Faculty of Pharmacy, Takasaki University of Health and Welfare, Takasaki, Japan
- 3 Laboratory of Molecular Design Chemistry, Faculty of Pharmacy, Takasaki University of Health and Welfare, Takasaki, Japan
- 4 Laboratory of Medicinal Chemistry, Faculty of Pharmacy, Takasaki University of Health and Welfare, Takasaki, Japan
- 5 Laboratory of Organic Chemistry, Faculty of Pharmaceutical Sciences, Sojo University, Kumamoto, Japan
Green and Sustainable Chemistry·Volume 12 (2022)·Pages 83–90·Published 11 November 2022·DOI10.4236/gsc.2022.124007
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Abstract
Protecting groups often play an essential role in organic synthesis, particularl y for multi-step synthesis or natural product total synthesis. Various protecting groups areavailable to mask the vulnerable functionality; phenolic hydroxy groups are noteworthy examples, but their stability differs when protected. Herein, the compatibility of protective phenolic functionality was investigated with the implementation of indium (III) triflate-catalyzed oxidative esterification using Oxone in methanol. A wide range of protective moieties was selected and subjected to Oxone-mediated oxidative esterification. For example, sulfonates were found to be sufficiently stable and inert whereas acetals were susceptible to reaction conditions. The details of this investigation are provided.
KeywordsCompatibilityProtecting GroupsPhenolic FunctionalityOxoneOxidative Esterification
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