催化分子间 [4+2]- 环加成实现吲哚的立体选择性 C2-C3 嵌合反应

Synthesis Pub Date : 2024-08-09 DOI:10.1055/a-2383-7416
Soumen Pandit, N. Majumdar
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引用次数: 0

摘要

与吲哚的 C2-C3 键进行催化脱芳香环化反应是合成融合吲哚啉支架的有力策略。通过脱芳香环化反应/嵌合反应,平面吲哚底物可以很容易地一步转化为刚性的三维多环复合结构。分子结构的复杂性通常被认为具有类似药物的特性。因此,环化产物在发现治疗特性方面具有巨大的潜力。这一策略已成为药物化学工具箱的重要组成部分。利用适当的催化剂控制,可以在反应中实现理想的立体选择性。以往的文献报道表明,对吲哚的 [3+2]-cycloaddition 反应进行了广泛的研究。相反,对吲哚的催化 [4+2]- 环加成/脱芳烃反应的研究则少得多。在本综述中,我们将特别关注通过[4+2]-环加成法与吲哚的 C2-C3 键进行六元环环化反应,并讨论朝这一方向发展的各种催化方法。
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Catalytic Intermolecular [4+2]-Cycloaddition toward Stereoselective C2-C3 Annulation of Indoles
Catalytic dearomative cycloaddition with C2-C3 bond of indoles is a powerful strategy for the synthesis of fused indoline scaffolds. By dearomative cycloaddition/annulation, planar indole substrates can be readily transformed into rigid, three-dimensional polycyclic complex structures in one step. Architectural complexity of molecules is generally considered as drug-like properties. Thus, the annulation products have tremendous potential in discovering therapeutic properties. This strategy has become an important part of the medicinal chemistry toolbox. Using appropriate catalyst control, desirable stereoselectivity can be achieved in the reaction. Previous literature reports indicate that [3+2]-cycloaddition of indoles has been extensively studied. On the contrary, catalytic [4+2]-cycloaddition/dearomatization of indoles has been much less investigated. In this review, we aim to focus specifically on the six- membered ring annulation via [4+2]-cycloaddition with C2-C3 bond of indoles and discuss on various catalytic methods that have been developed toward this direction.
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