CC BY-NC-ND 4.0 · Synthesis 2023; 55(11): 1770-1782
DOI: 10.1055/a-1993-6899
paper
Special Issue dedicated to Prof. Cristina Nevado, recipient of the 2021 Dr. Margaret Faul Women in Chemistry Award

Control over Stereogenic N–N Axes by Pd-Catalyzed 5-endo-Hydroaminocyclizations

Valeriia Hutskalova
,
Christof Sparr  ∗
We gratefully acknowledge the Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung (175746) and the National Centre of Competence in Research, Molecular Systems Engineering (NCCR MSE) (182895) for financial support. This project has received funding from the European Research Council (ERC) under the European Union’s Horizon 2020 (H2020) research and innovation programme (grant agreement No. 101002471).
› Further Information
   Permissions and Reprints All articles of this category


Dedicated to Prof. Cristina Nevado, recipient of the 2021 Dr. Margaret Faul Women in Chemistry Award

Abstract

A novel approach for the stereoselective construction of N–N atropisomeric compounds by a Pd-catalyzed 5-endo-hydroaminocyclization is described herein. A broad range of bisheterocycles , connected by a configurationally stable N–N stereogenic axis, were prepared with catalyst control in enantioenriched form.

Key words

palladium - cyclization - heterocycles - asymmetric catalysis - alkynes - atropisomers

Supporting Information



Publication History

Received: 23 September 2022

Accepted after revision: 06 December 2022

Accepted Manuscript online:
06 December 2022

Article published online:
16 January 2023

© 2022. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References

    • 1a Clayden J, Moran WJ, Edwards PJ, Laplante SR. Angew. Chem. Int. Ed. 2009; 48: 6398
      CrossrefPubMed
    • 1b Glunz PW. Bioorg. Med. Chem. Lett. 2018; 28: 53
      CrossrefPubMed
    • 1c Toenjes ST, Gustafson JL. Future Chem. 2018; 10: 409
      CrossrefPubMed
    • 2a Bringmann G, Gulder T, Gulder TA. M, Breuning M. Chem. Rev. 2011; 111: 563
      CrossrefPubMed
    • 2b Wencel-Delord J, Panossian A, Leroux FR, Colobert F. Chem. Soc. Rev. 2015; 44: 3418
      CrossrefPubMed
    • 2c Zilate B, Castrogiovanni A, Sparr C. ACS Catal. 2018; 8: 2981
      Crossref
  • 3 Gustafson JL, Lim D, Miller SJ. Science 2010; 328: 1251
    CrossrefPubMed
  • 4 Wang JZ, Zhou J, Xu C, Sun H, Kürti L, Xu QL. J. Am. Chem. Soc. 2016; 138: 5202
    CrossrefPubMed
  • 5 Rokade BV, Guiry PJ. ACS Catal. 2018; 8: 624
    CrossrefPubMed
  • 6 Sweetman BA, Guiry PJ. Tetrahedron 2018; 74: 5567
    Crossref
  • 7 Zhang P, Wang XM, Xu Q, Guo CQ, Wang P, Lu CJ, Liu RR. Angew. Chem. Int. Ed. 2021; 60: 21718
    CrossrefPubMed
  • 8 Rodríguez-Salamanca P, Fernández R, Hornillos V, Lassaletta JM. Chem. Eur. J. 2022; 28: e202104442
    CrossrefPubMed
  • 9 Di Iorio N, Righi P, Mazzanti A, Mancinelli M, Ciogli A, Bencivenni G. J. Am. Chem. Soc. 2014; 136: 10250
    CrossrefPubMed
  • 10 Hirai M, Terada S, Yoshida H, Ebine K, Hirata T, Kitagawa O. Org. Lett. 2016; 18: 5700
    CrossrefPubMed
  • 11 Bai HY, Tan FX, Liu TQ, Zhu GD, Tian JM, Ding TM, Chen ZM, Zhang SY. Nat. Commun. 2019; 10: 3063
    CrossrefPubMed
  • 12 Frey J, Malekafzali A, Delso I, Choppin S, Colobert F, Wencel-Delord J. Angew. Chem. Int. Ed. 2020; 59: 8844
    CrossrefPubMed
  • 13 Vaidya SD, Toenjes ST, Yamamoto N, Maddox SM, Gustafson JL. J. Am. Chem. Soc. 2020; 142: 2198
    CrossrefPubMed
  • 14 Chang C, Adams R. J. Am. Chem. Soc. 1931; 53: 2353
    CrossrefPubMed
    • 15a Xu Z, Baunach M, Ding L, Hertweck C. Angew. Chem. Int. Ed. 2012; 51: 10293
      CrossrefPubMed
    • 15b Zhang Q, Mándi A, Li S, Chen Y, Zhang W, Tian X, Zhang H, Li H, Zhang W, Zhang S, Ju J, Kurtán T, Zhang C. Eur. J. Org. Chem. 2012; 2012: 5256
      Crossref
    • 16a Dai J, Dan W, Schneider U, Wang J. Eur. J. Med. Chem. 2018; 157: 622
      CrossrefPubMed
    • 16b Blair LM, Sperry J. J. Nat. Prod. 2013; 76: 794
      CrossrefPubMed
  • 17 Liu XY, Zhang YL, Fei X, Liao LS, Fan J. Chem. Eur. J. 2019; 25: 4501
    CrossrefPubMed
  • 18 Antognazza P, Benincori T, Mazzoli S, Sannicolo F, Pilati T. Phosphorus, Sulfur Silicon Relat. Elem. 1999; 146: 405
    Crossref
  • 19 Mei GJ, Wong JJ, Zheng W, Nangia AA, Houk KN, Lu Y. Chem 2021; 7: 2743
    CrossrefPubMed
  • 20 Lin W, Zhao Q, Li Y, Pan M, Yang C, Yang GH, Li X. Chem. Sci. 2022; 13: 141
    CrossrefPubMed
  • 21 Pan M, Shao YB, Zhao Q, Li X. Org. Lett. 2022; 24: 374
    CrossrefPubMed
    • 22a Xu Q, Zhang H, Ge FB, Wang XM, Zhang P, Lu CJ, Liu RR. Org. Lett. 2022; 24: 3138
      CrossrefPubMed
    • 22b Wang XM, Zhang P, Xu Q, Guo CQ, Zhang DB, Lu CJ, Liu RR. J. Am. Chem. Soc. 2021; 143: 15005
      CrossrefPubMed
    • 23a Gao Y, Wang LY, Zhang T, Yang BM, Zhao Y. Angew. Chem. Int. Ed. 2022; 61: e202200371
      CrossrefPubMed
    • 23b Chen KW, Chen ZH, Yang S, Wu SF, Zhang YC, Shi F. Angew. Chem. Int. Ed. 2022; 61: e202116829
      CrossrefPubMed
    • 24a Portolani C, Centonze G, Luciani S, Pellegrini A, Righi P, Mazzanti A, Ciogli A, Sorato A, Bencivenni G. Angew. Chem. Int. Ed. 2022; 61: e202209895
      CrossrefPubMed
    • 24b Zhang P, Wang X.-M, Feng J, Lu C.-J, Li Y, Liu RR. Angew. Chem. Int. Ed. 2022; 61: e202212101
      CrossrefPubMed
    • 25a Ototake N, Morimoto Y, Mokuya A, Fukaya H, Shida Y, Kitagawa O. Chem. Eur. J. 2010; 16: 6752
      CrossrefPubMed
    • 25b Morimoto Y, Shimizu S, Mokuya A, Ototake N, Saito A, Kitagawa O. Tetrahedron 2016; 72: 5221
      Crossref
    • 26a Alsabeh PG, Lundgren RJ, Longobardi LE, Stradiotto M. Chem. Commun. 2011; 47: 6936
      CrossrefPubMed
    • 26b Halland N, Nazare M, Alonso J, R’Kyek O, Lindenschmidt A. Chem. Commun. 2011; 47: 1042
      CrossrefPubMed