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Elaboration of phosphoramidite ligands enabling palladium-catalyzed diastereo- and enantioselective all carbon [4+3] cycloaddition

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Abstract

A palladium-catalyzed diastereo- and enantioselective all carbon [4+3] cycloaddition of trimethylenemethane was developed by employing the elaborate tetrahydroquinoline-derived phosphoramidite ligand. The exclusive regioselectivity was realized by using the aromatization-driven diene indole-2,3-quinodimethanes, affording biologically important cyclohepta[b]indoles with excellent diastereo-, and enantioselectivities (up to >20:1 dr, >99% ee). Furthermore, the more challenging pyrrolidone-3,4-dienes, in the absence of aromatization force, were also compatible inthereaction, providing novel cyclohepta[c]pyrrol-1(2H)-ones with excellent regio-, diastereo-, and enantioselectivities (up to >20:1 rr, >20:1 dr, >99% ee).

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Acknowledgements

This work is supported by the National Natural Science Foundation of China (21772038, 21971062). We greatly appreciate the Research Center of Analysis and Test of East China University of Science and Technology for the assistance with the MS and NMR analysis.

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Authors and Affiliations

  1. Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, Shanghai, 200237, China

    Xing Zheng, Hao Sun, Wu-Lin Yang & Wei-Ping Deng

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  1. Xing Zheng
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  2. Hao Sun
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  3. Wu-Lin Yang
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  4. Wei-Ping Deng
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Correspondence to Wu-Lin Yang or Wei-Ping Deng.

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Zheng, X., Sun, H., Yang, WL. et al. Elaboration of phosphoramidite ligands enabling palladium-catalyzed diastereo- and enantioselective all carbon [4+3] cycloaddition. Sci. China Chem. 63, 911–916 (2020). https://doi.org/10.1007/s11426-020-9718-2

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  • DOI: https://doi.org/10.1007/s11426-020-9718-2

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