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Quinine-derived thiourea promoted enantioselective Michael addition reactions of 3-substituted phthalides to maleimides

  • Jie Wang
  • Xin Li
  • Jin-Pei Cheng
Articles
  • 14 Downloads

Abstract

A highly diastereoselective and enantioselective Michael addition/desymmetrization reaction of maleimides with prochiral 3- substituted phthalides catalyzed by quinine-derived bifunctional thiourea was realized. A broad range of the 3,3′-disubstituted phthalides bearing vicinal quaternary-tertiary stereogenic centers were synthesized in moderate to good yields (up to 96%) with high diastereoselectivities (up to >19:1 dr) and enantioselectivities (up to 96:4 er).

Keywords

michael addition 3,3′-disubstituted phthalides vicinal quaternary-tertiary stereogenic centers 

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Notes

Acknowledgements

This work was supported by the National Natural Science Foundation of China (21390400).

Supplementary material

11426_2018_9393_MOESM1_ESM.pdf (17.6 mb)
Supporting Information

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Copyright information

© Science China Press and Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  1. 1.State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, College of ChemistryNankai UniversityTianjinChina

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