Conjugate Addition−Enantioselective Protonation of N-Aryl Glycines to α-Branched 2-Vinylazaarenes via Cooperative Photoredox and Asymmetric Catalysis,Journal of the American Chemical Society

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Conjugate Addition−Enantioselective Protonation of N-Aryl Glycines to α-Branched 2-Vinylazaarenes via Cooperative Photoredox and Asymmetric Catalysis
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2018-04-10 , DOI: 10.1021/jacs.8b01575
Yanli Yin _{1,

2} , Yating Dai ₁ , Hongshao Jia ₁ , Jiangtao Li ₁ , Liwei Bu ₁ , Baokun Qiao ₁ , Xiaowei Zhao ₁ , Zhiyong Jiang ₁

Affiliation

An enantioselective protonation strategy has been successfully applied to the synthesis of chiral α-tertiary azaarenes. With a dual catalytic system involving a chiral phosphoric acid and a dicyanopyrazine-derived chromophore (DPZ) photosensitizer that is mediated by visible light, a variety of α-branched 2-vinylpyridines and 2-vinylquinolines with N-aryl glycines underwent a redox-neutral, radical conjugate addition-protonation process and provided valuable chiral 3-(2-pyridine/quinoline)-3-substituted amines in high yields with good to excellent enantioselectivities (up to >99% ee). An application of this methodology to a two-step synthesis of the enantiomerically pure medicinal compound pheniramine (Avil) is also presented.

中文翻译：

N-芳基甘氨酸通过协同光氧化还原和不对称催化共轭加成-对映选择性质子化为α-支链2-乙烯基氮杂芳烃

对映选择性质子化策略已成功应用于手性α-叔氮杂芳烃的合成。使用由可见光介导的手性磷酸和二氰基吡嗪衍生的发色团 (DPZ) 光敏剂的双重催化系统，各种 α-支链 2-乙烯基吡啶和 2-乙烯基喹啉与 N-芳基甘氨酸发生氧化还原反应，自由基共轭加成 - 质子化过程，并以高产率提供有价值的手性 3-（2-吡啶/喹啉）-3-取代胺，具有良好到出色的对映选择性（高达> 99％ee）。还介绍了该方法在对映异构纯药用化合物苯那敏 (Avil) 的两步合成中的应用。

更新日期：2018-04-10

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