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Asymmetric Ir-catalyzed hydrogenation of 1,5-benzodiazepinones using mixtures of ligands

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Abstract

The catalytic hydrogenation of benzodiazepinones using metal complexes with phosphite and phosphoramidite ligands was carried out for the first time. The mixed-ligand catalytic systems containing a chiral phosphoramidite or phosphite in combination with an achiral phosphine were shown to exhibit a higher enantioselectivity compared to catalysts containing homocombinations of chiral ligands.

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References

  1. J. Liu, A. C. Cheng, H. L. Tang, J. C. Medina, ACS Med. Chem. Lett., 2011, 2, 515.

    Article  CAS  Google Scholar 

  2. A. M. Taylor, A. Cote, M. C. Hewit, R. Pastor, Y. Leblanc, C. G. Nasveschuk, F. A. Romero, T. D. Crawford, N. Cantone, H. Jayaram, J. Setser, J. Murray, M. H. Beresini, G. de Leon Boenig, Z. Chen, A. R. Conery, R. T. Cummings, L. A. Dakin, E. M. Flynn, O. W. Huang, S. Kaufman, P. J. Keller, J. R. Kiefer, T. Lai, Y. Li, J. Liao, W. Liu, H. Lu, E. Pardo, V. Tsui, J. Wang, Y. Wang, Z. Xu, F. Yan, D. Yu, L. Zawadzke, X. Zhu, X. Zhu, R. J. Sims III, A. G. Cochran, S. Bellon, J. E. Audia, S. Magnuson, B. K. Albrecht, ACS Med. Chem. Lett., 2016, 7, 531.

    Article  CAS  Google Scholar 

  3. H. Zou, A. S. Limpert, J. Zou, A. Dembo, P. S. Lee, D. Grant, R. Ardecky, A. B. Pinkertone, G. K. Manguson, M. E. Goldman, J. Rong, P. Teriete, D. J. Sheffler, J. C. Reed, N. D. Cosford, ACS Chem. Neurosсi, 2015, 6, 464.

    Article  CAS  Google Scholar 

  4. M. Rueping, E. Merino, R. M. Koenigs, Adv. Synth. Catal., 2010, 352, 2629.

    Article  CAS  Google Scholar 

  5. X. Chen, Y. Zheng, Chang Shu, W. Yuan, B. Liu, X. Zhang, J. Org. Chem., 2011, 76, 9109.

    Article  CAS  Google Scholar 

  6. L. A. Nguyen, H. He, C. Pham-Huy, Int. J. Biomed. Sci., 2006, 2, 85.

    CAS  Google Scholar 

  7. P. van Leeuwen, P. Kamer, C. Claver, O. Pamies, M. Dieguez, Chem. Rev., 2011, 111, 2077.

    Article  Google Scholar 

  8. M.-T. Reetz, X. Li, Chem. Commun., 2006, 2159.

    Google Scholar 

  9. N. Mrsic, L. Lefort, J. A. F. Boogers, A. J. Minnaard, B. L. Feringa, J. G. de Vries, Adv. Synth. Catal., 2008, 350, 1081.

    Article  CAS  Google Scholar 

  10. X. Wang, Z. Li, X. Zhu, H. Mao, X. Zou, L. Kong, X. Li, Tetrahedron, 2008, 64, 6510.

    Article  CAS  Google Scholar 

  11. H. Mtiraoui, R. Gharbi, M. Msaddek, Y. Bretonnière, C. Andraud, C. Sabot, P.-Y. Renard, J. Org. Chem., 2016, 81, 4720.

    Article  CAS  Google Scholar 

  12. N. Mrsic, A. J. Minnaard, B. L. Feringa, J. G. de Vries, J. Am. Chem. Soc., 2009, 131, 8358.

    Article  CAS  Google Scholar 

  13. S. Woodward, WO Pat. 2007/036701 A1.

  14. J. L. Herde, J. C. Lambert, C. V. Senoff, Inorg. Synth., 1974, 15, 18.

    CAS  Google Scholar 

  15. P. Goswami, B. Das, Synthetic Commun., 2010, 40, 1685.

    Article  CAS  Google Scholar 

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Correspondence to S. E. Lyubimov.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1059—1061, June, 2017.

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Lyubimov, S.E., Ozolin, D.V. & Davankov, V.A. Asymmetric Ir-catalyzed hydrogenation of 1,5-benzodiazepinones using mixtures of ligands. Russ Chem Bull 66, 1059–1061 (2017). https://doi.org/10.1007/s11172-017-1853-1

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  • DOI: https://doi.org/10.1007/s11172-017-1853-1

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