动力学拆分在催化不对称1,3-偶极环加成反应中的研究进展
收稿日期: 2022-05-22
修回日期: 2022-06-25
网络出版日期: 2022-07-05
基金资助
国家自然科学基金(22071186); 国家自然科学基金(22101216); 湖北省自然科学基金(2020CFA036); 中国博士后科研基金(2021M702514); 中央高校基本科研业务费专项资金(2042022kf1180)
Recent Advances in Catalytic Asymmetric 1,3-Dipolar Cycloaddition Reactions with Kinetic Resolution
Received date: 2022-05-22
Revised date: 2022-06-25
Online published: 2022-07-05
Supported by
National Natural Science Foundation of China(22071186); National Natural Science Foundation of China(22101216); Natural Science Foundation of Huibei Province(2020CFA036); China Postdoctoral Science Foundation(2021M702514); Fundamental Research Funds for the Central Universities(2042022kf1180)
动力学拆分是一类高效且应用广泛的不对称有机合成策略, 可将外消旋化合物转化成高光学活性的构筑模块, 是现代不对称合成领域的重要组成部分. 尽管多年前就已被报道, 但涉及不对称催化的动力学拆分过程在实际运用中往往拆分效率较低或者底物适用范围较窄, 这极大地阻碍了该策略的发展. 过去的二十年里, 随着不对称催化领域中手性催化剂和手性配体的快速发展, 动力学拆分策略开始广泛运用于外消旋底物的高效分离, 进而获得优异光学纯度的手性分子. 自2005年亚甲胺亚胺通过催化不对称1,3-偶极环加成反应实现动力学拆分的案例被首次报道以来, 利用1,3-偶极环加成反应以实现高效动力学拆分获取手性氮杂环化合物或高对映选择性片段的相关研究已得到较好发展. 根据参与的1,3-偶极子的不同, 总结了近年来动力学拆分策略在亚甲胺亚胺和亚甲胺叶立德参的催化不对称1,3-偶极环加成反应中的研究进展, 并讨论了相关局限性和发展前景.
关键词： 动力学拆分; 不对称1,3-偶极环加成; 亚甲胺亚胺; 亚甲胺叶立德; 手性氮杂环
刘华超 , 沈冲 , 常鑫 , 王春江 . 动力学拆分在催化不对称1,3-偶极环加成反应中的研究进展[J]. 有机化学, 2022 , 42(10) : 3322 -3334 . DOI: 10.6023/cjoc202205037
Kinetic resolution is an efficient and widely used asymmetric organic synthesis strategy, which can transform racemic compounds into highly optically active building blocks. It is quite an important part of modern asymmetric synthesis. Although it has long been known as a common method to gain enantioenriched raw material, kinetic resolution processes involving asymmetric catalysis often show poor resolution efficiency and limited substrates scope in practice, which greatly hinder the development of this strategy. It is not until the past two decades, with the rapid development of chiral ligands and catalysts in the field of asymmetric catalysis, that kinetic resolution strategy has been increasingly applied in the efficient separation of racemic substrates to provide versatile chiral molecules with excellent optical purity. Since the strategy of kinetic resolution was first successfully employed in the catalytic asymmetric 1,3-dipolar cycloadditions with azomethine imines in 2005, studies on 1,3-dipolar cycloadditions with efficient kinetic resolution to achieve chiral N-heterocyclic compounds or highly enantioselective fragments have been well developed. The recent progress of kinetic resolution strategy in catalytic asymmetric 1,3-dipolar cycloaddition reactions involving azomethine imines and azomethine ylides is summarized according to the different azomethine 1,3-dipoles involved, and the related limitations and development prospects are also discussed.
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