Enantioselective Allylation of Oxocarbenium Ions Catalyzed by Bi(OAc)3/Chiral Phosphoric Acid,ACS Catalysis

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Enantioselective Allylation of Oxocarbenium Ions Catalyzed by Bi(OAc)3/Chiral Phosphoric Acid
ACS Catalysis ( IF 11.3 ) Pub Date : 2020-07-08 , DOI: 10.1021/acscatal.0c02585
Yu-Liang Pan ₁ , Han-Liang Zheng ₁ , Jie Wang ₁ , Chen Yang ₁ , Xin Li ₁ , Jin-Pei Cheng ₁

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Phthalides as the crucial core skeletons are found extensively in natural products and biological active molecules. Herein we disclose an asymmetric allylation of 3-hydroxyisobenzofuran-1(3H)-ones with boron allylation reagents to construct chiral phthalide derivatives. The simple Bi(OAc)₃/chiral phosphoric acid catalytic system proves to be efficient in this method, delivering the desired chiral 3-allylisobenzofuran-1(3H)-ones in good yields (up to 99%) and high enantioselectivities (up to 99.5:0.5 e.r.) under mild conditions. The large-scale reaction and diverse transformations of products to various scaffolds with potential biological activities render it more attractive. Moreover, the mechanism was preliminarily explored by control reactions, mass spectrometry, deuterium experiment, and DFT calculations.

中文翻译：

Bi（OAc）₃ /手性磷酸催化氧碳鎓离子的对映选择性烯丙基化

邻苯二甲酸酯作为关键的核心骨架广泛存在于天然产物和生物活性分子中。本文中我们公开了3-羟基异苯并呋喃-1（3H）-与硼烯丙基化试剂的不对称烯丙基化，以构建手性邻苯二甲酸酯衍生物。简单的Bi（OAc）₃ /手性磷酸催化体系在该方法中被证明是有效的，可提供所需的手性3-烯丙基苯并呋喃-1（3 H-在温和条件下收率高（高达99％）和高对映选择性（高达99.5：0.5 er）的化合物。产品的大规模反应和向具有潜在生物活性的各种支架的多样化转化使其更具吸引力。此外，通过控制反应，质谱，氘实验和DFT计算初步探讨了该机理。

更新日期：2020-08-08

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