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DOI: 10.1055/a-2099-6478
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Exploring the Power of Sulfur, Silicon, and Organocatalysis: Innovative Strategies for Asymmetric Synthesis and Advanced Synthetic Methodology

Kuei-Wei Chiu
a   Institute of Chemistry, Academia Sinica, Taipei 11529, Taiwan
,
Rong-Jie Chein∗
a   Institute of Chemistry, Academia Sinica, Taipei 11529, Taiwan
b   Biomedical Translation Research Center, Academia Sinica, Taipei 11529, Taiwan
› Author AffiliationsThis work was financially supported by Academia Sinica and the National Science and Technology Council (Taiwan) (109-2113-M001-035-MY3).
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Abstract

This research Account describes the development of chiral organocatalysts, focusing on diphenyl-2-pyrrolidinemethanol and its derivatives as valuable tools in asymmetric transformations. The research also includes the discovery of a novel anionic Si→C alkyl migration method, which has been developed into a one-pot procedure for synthesizing (E)-chalcones from hydroxyamide and N,N-diethylcarbamates. The findings underscore the potential of sulfide and silicon as valuable reagents for organic synthesis and emphasize the importance of exploring new reaction pathways and mechanisms to discover novel synthetic methods.

1 Introduction

2 Synthesis of 2 and Sulfur Reagent as Chiral Lewis Acid

3 Sulfur/Selenium Reagent as Chiral Lewis Base

4 Anionic Si→C Alkyl Migration

5 Conclusion

Key words

asymmetric catalysis - organocatalysis - oxathiaborolium - chiral sulfide - chiral selenide - alkyl migration - anionic Snieckus–Fries rearrangement


Publication History

Received: 21 April 2023

Accepted after revision: 24 May 2023

Accepted Manuscript online:
24 May 2023

Article published online:
06 September 2023

© 2023. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References

  • 1 Kapfhammer J, Matthes A. Hoppe-Seyler’s Z. Physiol. Chem. 1934; 223: 43
    Crossref
    • 2a Corey E, Bakshi RK, Shibata S. J. Am. Chem. Soc. 1987; 109: 5551
      CrossrefPubMed
    • 2b Hu Q.-Y, Zhou G, Corey E. J. Am. Chem. Soc. 2004; 126: 13708
      CrossrefPubMed
  • 3 Marigo M, Wabnitz TC, Fielenbach D, Jørgensen KA. Angew. Chem. Int. Ed. 2005; 117: 804
    CrossrefPubMed
  • 4 Hayashi Y, Gotoh H, Hayashi T, Shoji M. Angew. Chem. Int. Ed. 2005; 44: 4212
    CrossrefPubMed
  • 5 Franzén J, Marigo M, Fielenbach D, Wabnitz TC, Kjærsgaard A, Jørgensen KA. J. Am. Chem. Soc. 2005; 127: 18296
    CrossrefPubMed
  • 6 Shiina I, Konishi K, Kuramoto Y.-s. Chem. Lett. 2002; 31: 164
    CrossrefPubMed
  • 7 Wu H.-Y, Chang C.-W, Chein R.-J. J. Org. Chem. 2013; 78: 5788
    CrossrefPubMed
    • 8a Imanieh H, Quayle P, Voaden M, Conway J, Street SD. A. Tetrahedron Lett. 1992; 33: 543
      Crossref
    • 8b Macdonald JE, Poindexter GS. Tetrahedron Lett. 1987; 28: 1851
      Crossref
  • 9 Bavikar SR, Lo H.-J, Pavan Kumar CN. S. S, Chein R.-J. Chem. Commun. 2022; 58: 8564
    CrossrefPubMed
  • 11 Kumar SN, Bavikar SR, Pavan Kumar CN. S. S, Yu IF, Chein R.-J. Org. Lett. 2018; 20: 5362
    CrossrefPubMed
  • 12 Hayashi Y, Rohde JJ, Corey EJ. J. Am. Chem. Soc. 1996; 118: 5502
    CrossrefPubMed
  • 14 De Vries TS, Prokofjevs A, Vedejs E. Chem. Rev. 2012; 112: 4246
    CrossrefPubMed
  • 16 Mukhopadhyay S, Boobalan R, Chein R.-J. Org. Biomol. Chem. 2022; 20: 8405
    CrossrefPubMed
  • 17 Huang M.-T, Wu H.-Y, Chein R.-J. Chem. Commun. 2014; 50: 1101
    CrossrefPubMed
  • 18 Wang S.-H, Chein R.-J. Tetrahedron 2016; 72: 2607
    CrossrefPubMed
  • 19 Guo Y.-C, Chiu K.-W, Chein R.-J. J. Org. Chem. 2023; 88: 559
    CrossrefPubMed
  • 20 Cheng P.-T, Tseng Y.-H, Chein R.-J. Org. Lett. 2021; 23: 8104
    CrossrefPubMed
    • 21a Kamigata N, Nakamura Y, Kikuchi K, Ikemoto I, Shimizu T, Matsuyama H. J. Chem. Soc., Perkin Trans. 1 1992; 1721
      Crossref
    • 21b Takahashi T, Kurose N, Kawanami S, Nojiri A, Arai Y, Koizumi T, Shiro M. Chem. Lett. 1995; 24: 379
      Crossref