Unified Enantioselective Allylations and Vinylogous Reactions Enabled by Visible Light-Driven Chiral Lewis Acid Catalysis

IF 11.3 1区化学 Q1 CHEMISTRY, PHYSICAL

ACS Catalysis Pub Date : 2024-10-23 DOI:10.1021/acscatal.4c0463810.1021/acscatal.4c04638

Fuyuan Li, Fa-Yu Liu, Xiaowei Zhao*, Yanli Yin, Bin Yu, Junmin Zhang* and Zhiyong Jiang*,

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Abstract

In contemporary organic synthesis, chemists actively pursue a diverse range of substrates that can be efficiently catalyzed within an integrated system, playing a crucial role in advancing the pharmaceutical industry. However, due to the influence of substituents on reactivity and selectivity, it poses a challenging dilemma to explore different strategies for activating substrates with distinct functional groups. Herein, we have developed an important visible light-driven chiral Lewis acid catalysis platform which facilitates the unified allylations and vinylogous reactions of various allyl bromides and isatins for the highly enantio- and diastereoselective construction of valuable 3-allyl-3-hydroxy oxindoles. The success of this approach lies in utilizing a radical pathway for intermediate formation and stereocenter generation. Moreover, the activation capability of chiral Lewis acids provides an opportunity to achieve sufficient enantiocontrol and enhance regioselectivity. The robustness of this method is demonstrated by its application in precise radical-based propargylation reactions using readily accessible propargyl bromides.

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通过可见光驱动的手性路易斯酸催化实现统一的对映选择性烯丙基化和乙烯基化反应

在当代的有机合成中，化学家们积极寻求能在集成系统中高效催化的各种底物，这对推动制药业的发展起着至关重要的作用。然而，由于取代基对反应活性和选择性的影响，探索不同的策略来活化具有不同官能团的底物是一个极具挑战性的难题。在此，我们开发了一种重要的可见光驱动手性路易斯酸催化平台，该平台可促进各种烯丙基溴和异汀的统一烯丙基化和乙烯基化反应，从而高度对映和非对映选择性地构建有价值的 3- 烯丙基-3-羟基吲哚。这种方法的成功之处在于利用自由基途径形成中间体和生成立体中心。此外，手性路易斯酸的活化能力为实现充分的对映控制和提高区域选择性提供了机会。这种方法在基于自由基的精确丙炔化反应中的应用证明了它的稳健性，该反应使用的是容易获得的丙炔溴化物。

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来源期刊

ACS Catalysis CHEMISTRY, PHYSICAL-

CiteScore

20.80

自引率

6.20%

发文量

1253

审稿时长

1.5 months

期刊介绍： ACS Catalysis is an esteemed journal that publishes original research in the fields of heterogeneous catalysis, molecular catalysis, and biocatalysis. It offers broad coverage across diverse areas such as life sciences, organometallics and synthesis, photochemistry and electrochemistry, drug discovery and synthesis, materials science, environmental protection, polymer discovery and synthesis, and energy and fuels. The scope of the journal is to showcase innovative work in various aspects of catalysis. This includes new reactions and novel synthetic approaches utilizing known catalysts, the discovery or modification of new catalysts, elucidation of catalytic mechanisms through cutting-edge investigations, practical enhancements of existing processes, as well as conceptual advances in the field. Contributions to ACS Catalysis can encompass both experimental and theoretical research focused on catalytic molecules, macromolecules, and materials that exhibit catalytic turnover.