Kinetic Resolution of Cyclic Secondary Azides, Using an Enantioselective Copper-Catalyzed Azide-Alkyne Cycloaddition

Alexander Juliana R.; Ott Amy A.; Liu En-Chih; Topczewski Joseph J.

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Kinetic Resolution of Cyclic Secondary Azides, Using an Enantioselective Copper-Catalyzed Azide-Alkyne Cycloaddition

机译：循环仲叠氮化物的动力学分辨率，使用对映选择性的铜催化的叠氮化物 - 炔烃环加入

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An enantioselective copper-catalyzed azide-alkyne cycloaddition (E-CuAAC) is reported by kinetic resolution. Chiral triazoles were isolated in high yield with limiting alkyne (up to 97:3 enantiomeric ratio (er)). A range of substrates were tolerated (>30 examples), and the reaction was scaled to >1 g. The er of a triazole product could be enhanced by recrystallization and the recovered scalemic azide could be racemized and recycled. Recycling the azide allows efficient use of the undesired azide enantiomer.

机译：通过动力学分辨率报道了一种对映选择性的铜催化的叠氮化物 - 炔环加油（E-CUAAC）。用限制炔烃（高达97：3对映体比（ER））高产量分离手性三唑。耐受一系列底物（> 30实例），并将反应缩放至> 1g。通过重结晶可以增强三唑产物的ER，并且回收的崩解叠氮化物可以是外向化和再循环的。再循环叠氮允许有效地使用不需要的叠氮化物。

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《Organic letters》 |2019年第11期|共4页
作者
Alexander Juliana R.; Ott Amy A.; Liu En-Chih; Topczewski Joseph J.;
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Univ Minnesota Twin Cities Dept Chem Minneapolis MN 55455 USA;

Univ Minnesota Twin Cities Dept Chem Minneapolis MN 55455 USA;

Univ Minnesota Twin Cities Dept Chem Minneapolis MN 55455 USA;

Univ Minnesota Twin Cities Dept Chem Minneapolis MN 55455 USA;

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正文语种 eng
中图分类有机化学;
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1. Kinetic Resolution of Cyclic Secondary Azides, Using an Enantioselective Copper-Catalyzed Azide-Alkyne Cycloaddition [J] . Alexander Juliana R., Ott Amy A., Liu En-Chih, Organic letters . 2019,第11期

机译：循环仲叠氮化物的动力学分辨率，使用对映选择性的铜催化的叠氮化物 - 炔烃环加入
2. Enantioselective Copper-Catalyzed Azide-Alkyne Click Cycloaddition to Desymmetrization of Maleimide-Based Bis(alkynes) [J] . Song Tao, Li Li, Zhou Wei, Chemistry: A European journal . 2015,第2期

机译：对映选择性铜催化的叠氮化物-炔烃点击环加成反应对马来酰亚胺基双炔的不对称化
3. Decoration of Coiled-Coil Peptides with N-Cysteine Peptide Thioesters As Cyclic Peptide Precursors Using Copper-Catalyzed Azide-Alkyne Cycloaddition (CuAAC) Click Reaction [J] . Rink W. Mathis, Thomas Franziska Organic letters . 2018,第23期

机译：用铜催化叠氮化物 - 炔烃环加入（CUAAC）作为环状肽前体用N-半胱氨酸肽染色剂的装饰
4. Waterborne Non-Isocyanate Polyurethanes Cured via Azide-Alkyne Cycloaddition [C] . Bayley Peoples, Jie Wu, Robson Storey Annual international waterborne, high-solids, and powder coatings symposium . 2020

机译：水性非异氰酸酯聚氨酯通过叠氮化物 - 炔烃环加成固化
5. Star and cyclic shaped macromoleculars architectures prepared using copper-catalyzed azide-alkyne cycloaddition: Synthesis, purification and characterization. [D] . Zhang, Boyu. 2015

机译：使用铜催化的叠氮化物-炔烃环加成反应制备的星形和环状高分子结构：合成，纯化和表征。
6. Synthesis of (123-triazol-4-yl)methyl Phosphinates and (123-Triazol-4-yl)methyl Phosphates by Copper-Catalyzed Azide-Alkyne Cycloaddition [O] . Anna Tripolszky, Krisztina Németh, Pál Tamás Szabó, 2019

机译：铜催化的叠氮化物-炔烃环加成反应合成（123-三唑-4-基）甲基磷酸酯和（123-三唑-4-基）甲基磷酸酯
7. Kinetic Resolution of Cyclic Secondary Azides, Using an Enantioselective Copper-Catalyzed Azide–Alkyne Cycloaddition [O] . Juliana R. Alexander, Amy A. Ott, En-Chih Liu, 2019

机译：循环仲叠氮化物的动力学分辨率，使用对映选择性的铜催化的叠氮化物 - 炔烃环加入

Kinetic Resolution of Cyclic Secondary Azides, Using an Enantioselective Copper-Catalyzed Azide-Alkyne Cycloaddition

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