手性交换和相转移催化构建 C-C 轴手性喹唑啉酮
Enantioselective Construction of C-C Axially Chiral Quinazolinones via Chirality Exchange and Phase-Transfer Catalysis.
机构信息
State Key Laboratory for Oxo Synthesis and Selective Oxidation, Center for Excellence in Molecular Synthesis, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou 730000, China.
University of Chinese Academy of Sciences, Beijing 100049, P. R. China.
出版信息
Org Lett. 2021 Mar 5;23(5):1731-1737. doi: 10.1021/acs.orglett.1c00156. Epub 2021 Feb 15.
A family of axially chiral quinazolinone-based heterobiaryls were constructed with high levels of enantiocontrol (up to 94% ee). Convergently, three different synthetic methods have been realized to prepare these valuable compounds including central-to-axial chirality transfer, dynamic kinetic resolution, and phase-transfer catalysis. Importantly, novel P,N-ligands with a π-π stacking can be derived from heterobiaryls by chirality exchange strategy or synthesized directly from complementary phase-transfer catalysis by using the inexpensive chiral quaternary ammonium salt.
一个具有轴手性的基于喹唑啉酮的杂联芳烃家族被构建出来，具有高水平的对映选择性（最高可达 94%ee）。同时，实现了三种不同的合成方法来制备这些有价值的化合物，包括中心到轴手性转移、动态动力学拆分和相转移催化。重要的是，通过手性交换策略，可以从杂联芳烃中衍生出具有π-π堆积作用的新型 P,N-配体，或者通过使用廉价的手性季铵盐直接从互补的相转移催化中合成。
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