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Cascade asymmetric dearomative cyclization reactions via transition-metal-catalysis

Nature Synthesis volume 1, pages 203–216 (2022)Cite this article

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Abstract

Catalytic asymmetric dearomatization (CADA) reactions offer an efficient strategy for directly converting aromatic compounds into chiral cyclic molecules. Cascade dearomative cyclization reactions are an important subclass of these transformations, providing rapid access to various polycyclic scaffolds. Given the wide existence of natural products and bioactive molecules with polyheterocyclic skeletons, cascade dearomative cyclization reactions of versatile heteroaromatic compounds are particularly attractive. In this Review, we discuss representative examples of cascade asymmetric dearomative cyclization reactions catalysed by transition-metal complexes (including Au, Ir, Pd, Cu, Rh, Ni, Zn, Ti and V complexes) from the past decade. Close attention is paid to the dearomative cyclization reactions of indoles and related heteroaromatic compounds, with an emphasis on the reaction mechanisms, substrate scope and applications in total synthesis, as well as limitations and possible future directions.

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Fig. 1: Selected bioactive molecules of polycyclic indolines and the four different types of cascade dearomative cyclization reactions.
Fig. 2: Au-catalysed [2 + 2] cyclization using indoles as nucleophiles.
Fig. 3: [3 + 2] cyclization using indoles as nucleophiles with either vinyl carbenes, carbonyl ylides, quinones, aziridines or donor–acceptor cyclopropanes.
Fig. 4: [4 + 2] cyclization using indoles as nucleophiles.
Fig. 5: [3 + 2] cyclization using indoles as electrophiles.
Fig. 6: Cyclization initiated with allylic or propargylic substitution reactions.
Fig. 7: Cyclization initiated with C-arylation and C–X (X = O, N) formation reactions.
Fig. 8: Visible-light-promoted [2 + 2] or [4 + 2] reactions.

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Acknowledgements

We thank the National Key R&D Program of China (2021YFA1500100), NSFC (21821002, 22031012, 91856201, 22171282), and Science and Technology Commission of Shanghai Municipality (19590750400, 21520780100) for generous financial support. Y.-Z.L. thanks the China Postdoctoral Science Foundation (2020M681439).

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  1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai, China

    Yang-Zi Liu, Hao Song, Chao Zheng & Shu-Li You

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Y.-Z.L., H.S., C.Z. and S.-L.Y. co-wrote the manuscript.

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Liu, YZ., Song, H., Zheng, C. et al. Cascade asymmetric dearomative cyclization reactions via transition-metal-catalysis. Nat Synth 1, 203–216 (2022). https://doi.org/10.1038/s44160-022-00039-y

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