在酮介导的氧化酯化过程中用于保护酚功能的基团的相容性

T. Mineno, Yukizi Suzuki, Tomoya Nobuta, Daiki Takano, Hisao Kansui
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引用次数: 1

摘要

保护基团在有机合成中起着重要的作用,特别是在多步合成或天然产物全合成中。各种保护组可用于掩盖易受攻击的功能;酚羟基是值得注意的例子,但它们的稳定性在保护时不同。本文研究了保护酚醛官能团与三氟化铟催化氧化酯化反应的相容性。广泛的保护基团被选择并受到氧酮介导的氧化酯化反应。例如,磺酸盐被发现是足够稳定和惰性的,而缩醛则易受反应条件的影响。提供了这项调查的细节。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
The Compatibility of Groups Used to Protect Phenolic Functionality during Oxone-Mediated Oxidative Esterification
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 pro-vided.
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