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P*,N-Bidentate bicyclic phosphoramidite: synthesis and catalytic testing

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Abstract

A new representative of novel chiral P*, N-bidentate bicyclic phosphoramidite ligands was synthesized. Palladium catalysts based on this ligand were tested in the asymmetric allylic alkylation of (E)-1,3-diphenylallyl acetate with dimethyl malonate and in the amination of the same substrate with pyrrolidine and demonstrated high activity (up to 100% conversion) and enantioselectivity up to 40% ee.

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References

  1. H. Shet, U. Parmar, S. Bhilare, A. R. Kapdi, Org. Chem. Front., 2021, 8, 1599; DOI: https://doi.org/10.1039/d0qo01194k.

    Article  CAS  Google Scholar 

  2. Y. Zhou, D. W. Armstrong, Y. Zhang, J. G. Verkade, Tetrahedron Lett., 2011, 52, 1545; DOI: https://doi.org/10.1016/j.tetlet.2011.01.041.

    Article  CAS  Google Scholar 

  3. J. You, A. E. Wro’blewski, J. G. Verkade, Tetrahedron, 2004, 60, 7877; DOI: https://doi.org/10.1016/j.tet.2004.06.115.

    Article  CAS  Google Scholar 

  4. Q. Xu, N. J. Dupper, A. J. Smaligo, Y. C. Fan, L. Cai, Z. Wang, A. D. Langenbacher, J.-N. Chen, O. Kwon, Org. Lett., 2018, 20, 6089; DOI: https://doi.org/10.1021/acs.orglett.8b02489.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  5. M. P. Carroll, P. J. Guiry, Chem. Soc. Rev., 2014, 43, 819; DOI: https://doi.org/10.1039/c3cs60302d.

    Article  CAS  PubMed  Google Scholar 

  6. B. V. Rokade, P. J. Guiry, ACS Catal., 2018, 8, 624; DOI: https://doi.org/10.1021/acscatal.7b03759.

    Article  CAS  Google Scholar 

  7. J. Margalef, M. Biosca, P. de la C. Sánchez, J. Faiges, O. Pàmies, M. Diéguez, Coord. Chem. Rev., 2021, 446, 214120; DOI: https://doi.org/10.1016/j.ccr.2021.214120.

    Article  CAS  Google Scholar 

  8. O. Pàmies, J. Margalef, S. Cañellas, J. James, E. Judge, P. J. Guiry, C. Moberg, J.-E. Bäckvall, A. Pfaltz, M. A. Pericàs, M. Diéguez, Chem. Rev., 2021, 121, 4373; DOI: https://doi.org/10.1021/acs.chemrev.0c00736.

    Article  PubMed  PubMed Central  Google Scholar 

  9. K. N. Gavrilov, I. S. Mikhel, S. V. Zheglov, V. K. Gavrilov, I. V. Chuchelkin, I. D. Firsin, K. P. Birin, I. S. Pytskii, K. A. Paseshnichenko, V. A. Tafeenko, V. V. Chernyshev, A. A. Shiryaev, Org. Chem. Front., 2019, 6, 1637; DOI: https://doi.org/10.1039/c9qo00237e.

    Article  CAS  Google Scholar 

  10. E. B. Benetskiy, C. Bolm, Tetrahedron: Asymmetry, 2011, 22, 373; DOI: https://doi.org/10.1016/j.tetasy.2011.02.005.

    Article  CAS  Google Scholar 

  11. K. E. Thiesen, K. Maitra, M. M. Olmstead, S. Attar, Organometallics, 2010, 29, 6334; DOI: https://doi.org/10.1021/om100741m.

    Article  CAS  Google Scholar 

  12. M. Ramillien, N. Vanthuyne, M. Jean, D. Gheraseb, M. Giorgic, J.-V. Naubronc, P. Piras, C. Roussel, J. Chromatogr., Part. A, 2012, 1269, 82; DOI: https://doi.org/10.1016/j.chroma.2012.09.025.

    Article  CAS  Google Scholar 

  13. K. N. Gavrilov, A. A. Shiryaev, S. V. Zheglov, V. K. Gavrilov, N. N. Groshkin, M. G. Maksimova, A. N. Volov, I. A. Zamilatskov, Tetrahedron, 2014, 70, 616; DOI: https://doi.org/10.1016/j.tet.2013.12.006.

    Article  CAS  Google Scholar 

  14. H. Brunner, S. Altmann, Chem. Ber., 1994, 127, 2285; DOI: https://doi.org/10.1002/cber.1491271130.

    Article  CAS  Google Scholar 

  15. P. R. Auburn, P. B. Mackenzie, B. Bosnich, J. Am. Chem. Soc., 1985, 107, 2033; DOI: https://doi.org/10.1021/ja00293a038.

    Article  CAS  Google Scholar 

  16. V. N. Tsarev, S. E. Lyubimov, A. A. Shiryaev, S. V. Zheglov, O. G. Bondarev, V. A. Davankov, A. A. Kabro, S. K. Moiseev, V. N. Kalinin, K. N. Gavrilov, Eur. J. Org. Chem., 2004, 2004, 2214; DOI: https://doi.org/10.1002/ejoc.200300694.

    Article  Google Scholar 

  17. K. N. Gavrilov, I. V. Chuchelkin, S. V. Zheglov, I. D. Firsin, V. S. Zimarev, V. K. Gavrilov, A. V. Maximychev, A. M. Perepukhov, N. S. Goulioukina, Mendeleev Commun., 2020, 30, 31; DOI: https://doi.org/10.1016/j.mencom.2020.01.010.

    Article  CAS  Google Scholar 

  18. S. Breeden, M. Wills, J. Org. Chem., 1999, 64, 9735; DOI: https://doi.org/10.1021/jo9912101.

    Article  CAS  Google Scholar 

  19. L.-Y. Mei, Z.-L. Yuan, M. Shi, Organometallics, 2011, 30, 6466; DOI: https://doi.org/10.1021/om2008309.

    Article  CAS  Google Scholar 

  20. D. Smyth, H. Tye, C. Eldred, N. W. Alcock, M. Wills, J. Chem. Soc., Perkin Trans. 1, 2001, 2840; DOI: https://doi.org/10.1039/B106399P.

  21. J. Chen, F. Lang, D. Li, L. Cun, J. Zhu, J. Deng, J. Liao, Tetrahedron: Asymmetry, 2009, 20, 1953; DOI: https://doi.org/10.1016/j.tetasy.2009.07.041.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. S. A. Yesenin Ryazan State University, 46 ul. Svobody, 390000, Ryazan, Russian Federation

    K. N. Gavrilov, I. V. Chuchelkin, V. M. Trunina, V. K. Gavrilov & I. D. Firsin

  2. Limited Liability Company R-Vekom, 20 ul. Lenina, 390000, Ryazan, Russian Federation

    V. M. Trunina, V. K. Gavrilov & I. D. Firsin

  3. A. V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, 29 Leninsky prosp., 119991, Moscow, Russian Federation

    E. V. Bermesheva

  4. I. M. Sechenov First Moscow State Medical University, Build. 2, 8 ul. Trubetskaya, 119992, Moscow, Russian Federation

    E. V. Bermesheva

Authors
  1. K. N. Gavrilov
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  2. I. V. Chuchelkin
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  3. V. M. Trunina
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  4. V. K. Gavrilov
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  5. I. D. Firsin
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  6. E. V. Bermesheva
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Corresponding author

Correspondence to K. N. Gavrilov.

Additional information

Dedicated to Academician of the Russian Academy of Sciences I. P. Beletskaya on the occasion of her anniversary.

This study was financially supported by the Russian Science Foundation (Project No. 22-23-20001, https://rscf.ru/project/22-23-20001) and by the Government of the Ryazan Region.

No human or animal subjects were used in this research.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 4, pp. 873–876, April, 2023.

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Gavrilov, K.N., Chuchelkin, I.V., Trunina, V.M. et al. P*,N-Bidentate bicyclic phosphoramidite: synthesis and catalytic testing. Russ Chem Bull 72, 873–876 (2023). https://doi.org/10.1007/s11172-023-3850-5

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  • DOI: https://doi.org/10.1007/s11172-023-3850-5

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