Enantioselective Copper Catalyzed Alkyne-Azide Cycloaddition by Dynamic Kinetic Resolution
Enantioselective Copper Catalyzed Alkyne-Azide Cycloaddition by Dynamic Kinetic Resolution
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DOI：
10.1021/jacs.9b01091
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发表时间：
2019-04-03
影响因子：
15
通讯作者：
Topczewski, Joseph J.
中科院分区：
文献类型：
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作者：
Liu, En-Chih;Topczewski, Joseph J.
铜（I）催化的炔-叠氮环加成（CuAAC）是一种点击反应，是近二十年来发展的最强的催化反应之一。对映选择性地进行CuAAC将为该反应增加第三个维度，并能够直接合成α-手性三唑。这样做是有要求的，因为两种前体具有线性几何形状，并且三唑产物是扁平杂环。由于CuAAC的复杂机理，手性催化剂的设计进一步复杂化。我们报告了一个对映选择性的CuAAC（E-CuAAC），使动态动力学拆分（DKR）。E-CuAAC产率高，产率可达99：1。E-CuAAC可在复杂的分子环境中直接生成α-手性三唑。
The copper(I) catalyzed alkyne-azide cycloaddition (CuAAC), a click reaction, is one of the most powerful catalytic reactions developed during the last two decades. Conducting CuAAC enantioselectively would add a third dimension to this reaction and would enable the direct synthesis of alpha-chiral triazoles. Doing so is demanding because the two precursors have linear geometries, and the triazole product is a flat heterocycle. Designing a chiral catalyst is further complicated by the complex mechanism of CuAAC. We report an enantioselective CuAAC (E-CuAAC), enabled by dynamic kinetic resolution (DKR). The E-CuAAC is high yielding and affords up to 99:1 er. The E-CuAAC can directly generate alpha-chiral triazoles in a complex molecular environment.