Chemoselective Asymmetric Intramolecular Dearomatization of Phenols with α-Diazoacetamides Catalyzed by Silver Phosphate,Journal of the American Chemical Society

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Chemoselective Asymmetric Intramolecular Dearomatization of Phenols with α-Diazoacetamides Catalyzed by Silver Phosphate
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2017-07-21 00:00:00 , DOI: 10.1021/jacs.7b04813
Hiroki Nakayama ₁ , Shingo Harada ₁ , Masato Kono ₁ , Tetsuhiro Nemoto _{1,

2}

Affiliation

We report asymmetric dearomatization of phenols using Ag carbenoids from α-diazoacetamides. The Ag catalyst promoted intramolecular dearomatization of phenols, whereas a Rh or Cu catalyst caused C–H insertion and a Büchner reaction. Studies indicated Ag carbenoids have a carbocation-like character, making their behavior and properties unique. Highly enantioselective transformations using Ag carbenoids have not been reported. We achieved a Ag carbenoid-mediated chemo- and highly enantioselective phenol dearomatization with substrate generality for the first time.

中文翻译：

磷酸银催化α-重氮乙酰胺对苯酚的化学选择性不对称分子内脱芳香化作用

我们报道了使用来自α-重氮乙酰胺的银类类胡萝卜素对苯酚的不对称脱芳香化作用。Ag催化剂促进了酚的分子内脱芳香化作用，而Rh或Cu催化剂则导致C–H插入和Büchner反应。研究表明，银类类胡萝卜素具有类似碳正离子的特性，因此其行为和特性具有独特性。尚未报道使用银类类胡萝卜素的高度对映选择性转化。我们首次实现了具有底物通用性的Ag类胡萝卜素介导的化学和高对映选择性苯酚脱芳香化作用。

更新日期：2017-07-22

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