Direct Construction of 1,3-Diaxial Diol Derivatives by C-H Hydroxylation
Direct Construction of 1,3-Diaxial Diol Derivatives by C-H Hydroxylation
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DOI：
10.1021/ol901367m
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发表时间：
2009-08-20
期刊：
影响因子：
5.2
通讯作者：
Inoue, Masayuki
中科院分区：
文献类型：
--
作者：
Kasuya, Satoshi;Kamijo, Shin;Inoue, Masayuki
通过设计一种包含三氟甲基酮部分和乙烯系链的新型可分离双环氧乙烷前体，实现了用于构建 1,3-二轴二醇衍生物的 C-H 叔键的直接羟基化。酮的过硫酸氢钠处理产生相应的二氧杂环己烷，通过分子内氧插入，使羟基以区域和立体选择性方式安装到环己烷和类固醇衍生物中。
Direct hydroxylation of tertiary C-H bonds for construction of 1,3-diaxial diol derivatives was achieved by devising a new detachable dioxirane precursor containing a trifluoromethyl ketone moiety and ethylene tether. Oxone treatment of the ketones led to the corresponding dioxiranes, enabling hydroxy group installment into cyclohexane and steroid derivatives in a regio- and stereoselective manner through intramolecular oxygen insertion.