Highly Discriminative and Chemoselective Deprotection/Transformations of Acetals with the Combination of Trialkylsilyl Triflate/2,4,6-Collidine
Highly Discriminative and Chemoselective Deprotection/Transformations of Acetals with the Combination of Trialkylsilyl Triflate/2,4,6-Collidine
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结合三氟甲磺酸三烷基甲硅烷酯/2,4,6-可力丁对缩醛进行高度辨别和化学选择性脱保护/转化
DOI：
10.1021/acs.joc.8b00675
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发表时间：
2018
影响因子：
3.6
通讯作者：
Hiromichi Fujioka
中科院分区：
文献类型：
--
作者：
Reiya Ohta;Nao Matsumoto;Yoshifumi Ueyama;Yuichi Kuboki;Hiroshi Aoyama;Kenichi Murai;Mitsuhiro Arisawa;Tomohiro Maegawa;Hiromichi Fujioka
缩醛是羰基官能团最有用的保护基团。除了保护作用外，它们还可以作为羰基功能的合成物。在此之前，我们开发了一种化学选择性脱保护和亲核取代醛在存在的缩醛。本文描述了具有不同取代模式的缩醛、不同类型的缩醛以及混合缩醛的高度判别性和化学选择性转化。这些反应可以实现传统方法无法实现的转变，并且他们的结果强烈表明R3SiOTf/2,4,6-碰撞的组合可以促进这种前所未有的现象。
Acetals are the most useful protecting groups for carbonyl functional groups. In addition to the role of protection, they can also be used as synthons of carbonyl functions. Previously, we developed a chemoselective deprotection and nucleophilic substitution of acetals from aldehydes in the presence of ketals. This article describes the highly discriminative and chemoselective transformations of acetals bearing different substitution patterns, different types of acetals, as well as mixed acetals. These reactions can achieve the transformations that cannot be attained by conventional methods, and their results strongly suggest the combination of R3SiOTf/2,4,6-collidine to promote such unprecedented phenomena.