The Compatibility of Groups Used to Protect Phenolic Functionality during Oxone-Mediated Oxidative Esterification  

作　　者：Tomoko Mineno Yuki Suzuki Tomoya Nobuta Daiki Takano Hisao Kansui Tomoko Mineno;Yuki Suzuki;Tomoya Nobuta;Daiki Takano;Hisao Kansui(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 Organic Chemistry, Faculty of Pharmaceutical Sciences, Sojo University, Kumamoto, Japan)

机构地区：[1]Laboratory of Medicinal Chemistry, Faculty of Pharmacy, Takasaki University of Health and Welfare, Takasaki, Japan [2]Laboratory of Molecular Design Chemistry, Faculty of Pharmacy, Takasaki University of Health and Welfare, Takasaki, Japan [3]Laboratory of Organic Chemistry, Faculty of Pharmaceutical Sciences, Sojo University, Kumamoto, Japan

出　　处：《Green and Sustainable Chemistry》2022年第4期83-90,共8页绿色与可持续化学（英文）

摘　　要：Protecting groups often play an essential role in organic synthesis, particularly 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.Protecting groups often play an essential role in organic synthesis, particularly 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.

关 键 词：Compatibility Protecting Groups Phenolic Functionality OXONE Oxidative Esterification 

分 类 号：O62[理学—有机化学]