Catalytic Enantioselective Carbon–Oxygen Bond Formation: Phosphine-Catalyzed Synthesis of Benzylic Ethers via the Oxidation of Benzylic C–H Bonds,Journal of the American Chemical Society

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Catalytic Enantioselective Carbon–Oxygen Bond Formation: Phosphine-Catalyzed Synthesis of Benzylic Ethers via the Oxidation of Benzylic C–H Bonds
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2016-09-12 , DOI: 10.1021/jacs.6b08486
Daniel T. Ziegler ₁ , Gregory C. Fu ₁

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Benzylic alcohols and ethers are common subunits in bioactive molecules, as well as useful intermediates in organic chemistry. In this Communication, we describe a new approach to the enantioselective synthesis of benzylic ethers through the chiral phosphine-catalyzed coupling of two readily available partners, γ-aryl-substituted alkynoates and alcohols, under mild conditions. In this process, the alkynoate partner undergoes an internal redox reaction. Specifically, the benzylic position is oxidized with good enantioselectivity, and the alkyne is reduced to the alkene.

中文翻译：

催化对映选择性碳-氧键形成：膦催化通过苄基 C-H 键氧化合成苄基醚

苯甲醇和醚是生物活性分子中常见的亚基，也是有机化学中有用的中间体。在这篇通讯中，我们描述了一种通过手性膦催化偶联两个容易获得的伙伴，γ-芳基取代的炔酸酯和醇，在温和条件下对映选择性合成苄醚的新方法。在这个过程中，炔酸伙伴进行内部氧化还原反应。具体而言，苄基位置以良好的对映选择性氧化，炔烃被还原为烯烃。

更新日期：2016-09-12

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