Diastereo- and Atroposelective Synthesis of Bridged Biaryls Bearing an Eight-Membered Lactone through an Organocatalytic Cascade,Journal of the American Chemical Society

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Diastereo- and Atroposelective Synthesis of Bridged Biaryls Bearing an Eight-Membered Lactone through an Organocatalytic Cascade
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2019-10-11 , DOI: 10.1021/jacs.9b08510
Shenci Lu _{1,

2} , Jun-Yang Ong _{1,

3} , Hui Yang ₁ , Si Bei Poh ₁ , Xi Liew ₁ , Chwee San Deborah Seow ₁ , Ming Wah Wong ₁ , Yu Zhao _{1,

4}

Affiliation

We present herein an unprecedented stereoselective synthesis of bridged biaryls with defined axial and central chirality from readily available starting materials. This NHC-catalyzed method proceeds through propargylic substitution of azolium enolates followed by two-directional cyclization as supported by DFT calculation. A range of benzofuran/indole-derived bridged biaryls bearing an eight-membered lactone are accessed with uniformly high stereoselectivity (>98:2 dr, mostly >98% ee).

中文翻译：

带有八元内酯的桥联联芳基化合物通过有机催化级联的非对映选择性和阻滞选择性合成

我们在本文中提出了一种前所未有的立体选择性合成，从容易获得的起始材料中合成具有确定的轴向和中心手性的桥联联芳基化合物。这种 NHC 催化的方法通过炔醇烯醇的炔丙基取代，然后在 DFT 计算的支持下进行双向环化。一系列带有八元内酯的苯并呋喃/吲哚衍生的桥联联芳基化合物以一致的高立体选择性（> 98:2 dr，大多数> 98% ee）获得。

更新日期：2019-10-11

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