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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

  • Qinghua Wei
  • Zi Li
  • Xi Yang
  • Jianghui Chen
  • Xiaohua Liu
  • Wenhao HuEmail author
  • Shunying LiuEmail author
Original Article
  • 29 Downloads

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).

Graphical abstract

Keywords

Rh(I)/Sc(III) co-catalyzed 1,4-diketone structural diversity Ammonium ylide Three-component reaction 

Notes

Acknowledgements

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

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

Supplementary material

11030_2019_9941_MOESM1_ESM.pdf (7.4 mb)
Supplementary material 1 (PDF 7587 kb)

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Copyright information

© Springer Nature Switzerland AG 2019

Authors and Affiliations

  1. 1.Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular EngineeringEast China Normal UniversityShanghaiChina
  2. 2.School of Pharmaceutical SciencesSun Yat-sen UniversityGuangzhouChina
  3. 3.Key Laboratory of Green Chemistry and Technology Ministry of Education, College of ChemistrySichuan UniversityChengduChina

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