Yang Gongming, Sun Shaofa, Li Zhipeng, Liu Yuhan, Wang Jian
School of Pharmaceutical Sciences, Key Laboratory of Bioorganic Phosphorous Chemistry and Chemical Biology (Ministry of Education), Tsinghua University, Beijing, 100084, China.
College of Chemistry and Biological Sciences, Hubei University of Science and Technology, Xianning, Hubei, 437100, China.
Commun Chem. 2021 Oct 13;4(1):144. doi: 10.1038/s42004-021-00580-5.
Axially chiral heterobiaryls play a vital role in asymmetric synthesis and drug discovery. However, there are few reports on the synthesis of atropisomeric heterobiaryls compared with axially chiral biaryls. Thus, the rapid enantioselective construction of optically active heterobiaryls and their analogues remains an attractive challenge. Here, we report a concise chiral amine-catalyzed atroposelective heterocycloaddition reaction of alkynes with ortho-aminoarylaldehydes, and obtain a new class of axially chiral 2-arylquinoline skeletons with high yields and excellent enantioselectivities. In addition, the axially chiral 2-arylquinoline framework with different substituents is expected to be widely used in enantioselective synthesis.
轴手性杂联芳基在不对称合成和药物发现中起着至关重要的作用。然而，与轴手性联芳基相比，关于阻转异构杂联芳基的合成报道较少。因此，快速对映选择性构建光学活性杂联芳基及其类似物仍然是一个具有吸引力的挑战。在此，我们报道了一种简洁的手性胺催化的炔烃与邻氨基芳基醛的对映选择性杂环加成反应，并以高产率和优异的对映选择性获得了一类新型的轴手性2-芳基喹啉骨架。此外，具有不同取代基的轴手性2-芳基喹啉骨架有望广泛应用于对映选择性合成。
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