具有乙炔基的功能性叔醇的高度对映选择性铜催化的叠氮化物-炔烃环加成反应及其动力学拆分
Highly Enantioselective CuAAC of Functional Tertiary Alcohols Featuring an Ethynyl Group and Their Kinetic Resolution.
作者信息
Liao Kui, Gong Yi, Zhu Ren-Yi, Wang Cai, Zhou Feng, Zhou Jian
机构信息
Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663N Zhongshan Road, Shanghai, 200062, China.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, P. R. China.
出版信息
Angew Chem Int Ed Engl. 2021 Apr 6;60(15):8488-8493. doi: 10.1002/anie.202016286. Epub 2021 Mar 1.
The first highly enantioselective Cu -catalyzed azide-alkyne cycloaddition (CuAAC) of tertiary alcohols and their kinetic resolution is reported. This approach allows facile access to multifunctional tertiary alcohols featuring an α-ethynyl or α-triazole moiety, and represents the first successful kinetic resolution of racemates with a tetrasubstituted carbon stereocenter via CuAAC. Newly developed pyridinebisoxazoline (PYBOX) ligands with a C4 phosphonate group play a key role.
报道了首例叔醇的高度对映选择性铜催化叠氮化物-炔烃环加成反应（CuAAC）及其动力学拆分。该方法能够方便地获得具有α-乙炔基或α-三唑部分的多功能叔醇，并且代表了通过CuAAC对具有四取代碳立体中心的外消旋体进行的首次成功动力学拆分。新开发的带有C4膦酸酯基团的吡啶双恶唑啉（PYBOX）配体起到了关键作用。
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