Catalytic, Enantioselective Diamination of Alkenes

Catalytic, Enantioselective Diamination of Alkenes
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DOI:
10.1055/s-0040-1719822
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发表时间:
2021-07
期刊:
Synthesis
影响因子:
--
通讯作者:
S. Denmark;Zhonglin Tao
S. Denmark;Zhonglin Tao
中科院分区:
其他
文献类型:
--
作者:
S. Denmark;Zhonglin Tao

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烯烃的对映选择性二化是获得对映富邻二胺最直接的方法之一,这不仅在生物活性化合物中经常遇到,而且在不对称合成中也有广泛的应用。虽然烯烃的类似二羟基化反应已经建立,但对映选择性烯烃二羟基化反应的发展远远滞后。然而,已经开发了几种成功的方法,这些方法通过不同的反应机制运作,包括环加成途径,双电子氧化还原途径和自由基途径。这篇简短的综述总结了最近的进展并指出了局限性,目的是激励这一领域的进一步发展。1简介2环加成途径3双电子氧化还原途径3.1 Pd(0)/Pd(II)二化3.2 Pd(II)/Pd(IV)二化3.3 I(I)/I(III)二化3.4 Se(II)/Se(IV)二化4单电子自由基途径4.1 cu催化二化4.2 fe催化二化5综述与展望
Abstract Enantioselective diamination of alkenes represents one of the most straightforward methods to access enantioenriched, vicinal diamines, which are not only frequently encountered in biologically active compounds, but also have broad applications in asymmetric synthesis. Although the analogous dihydroxylation of olefins is well-established, the development of enantioselective olefin diamination lags far behind. Nevertheless, several successful methods have been developed that operate by different reaction mechanisms, including a cycloaddition pathway, a two-electron redox pathway, and a radical pathway. This short review summarizes recent advances and identifies limitations, with the aim of inspiring further developments in this area. 1 Introduction 2 Cycloaddition Pathway 3 Two-Electron Redox Pathway 3.1 Pd(0)/Pd(II) Diamination 3.2 Pd(II)/Pd(IV) Diamination 3.3 I(I)/I(III) Diamination 3.4 Se(II)/Se(IV) Diamination 4 One-Electron Radical Pathway 4.1 Cu-Catalyzed Diamination 4.2 Fe-Catalyzed Diamination 5 Summary and Outlook