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Rh(I)/Sc(OTf)3-co-catalyzed Michael addition of ammonium ylide to (E)-1,4-enediones: synthesis of functionalized 1,4-diketones

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Abstract

A Rh(I)/Sc(III) co-catalyzed synthesis of highly valuable functionalized 1,4-diketone derivatives in good yields and with an excellent diastereoselectivity. The established method provides a rapid approach to structurally diverse 1,4-diketone scaffold in a very mild and rapid fashion from simple starting materials. Moreover, the protocol could be easily scaled up to gram-scale synthesis. An attempt to develop an asymmetric version of the Rh(I)/guanidine system was also explored, resulting in a moderate enantioselectivity (71% ee).

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Acknowledgements

We gratefully acknowledge the National Natural Science Foundation of China (Nos. 21332003 and 21672066).

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Authors and Affiliations

  1. Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200062, China

    Qinghua Wei, Zi Li, Xi Yang, Jianghui Chen & Shunying Liu

  2. School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, 510006, China

    Wenhao Hu

  3. Key Laboratory of Green Chemistry and Technology Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, China

    Xiaohua Liu

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  1. Qinghua Wei
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  2. Zi Li
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  3. Xi Yang
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Wei, Q., Li, Z., Yang, X. et al. Rh(I)/Sc(OTf)3-co-catalyzed Michael addition of ammonium ylide to (E)-1,4-enediones: synthesis of functionalized 1,4-diketones. Mol Divers 23, 997–1010 (2019). https://doi.org/10.1007/s11030-019-09941-8

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