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Asymmetric metal complex hydrogenation of 1-methyl-3,4-dihydroisoquinoline in the presence of amidophosphite ligand

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Abstract

A number of metal complex precatalysts, solvents, and additives were examined in the asymmetric hydrogenation of 1-methyl-3,4-dihydroisoquinoline in the presence of a chiral amidophosphite ligand. The enantioselectivity of hydrogenation of this substrate increased upon addition of iodine. The best result in the selective hydrogenation was observed when [Ir(COD)2]BARF was used as the precatalyst (COD is the cycloocta-1,5-diene, BARF is the tetrakis[3,5-bis(trifluoromethyl)phenyl]borate).

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References

  1. J. D. Phillipson, M. F. Roberts, M. H. Zenk, The Chemistry and Biology of Isoquinoline Alkaloids, Springer, Berlin, 1985.

    Book  Google Scholar 

  2. J. D. Scott, R. M. Williams, Chem. Rev., 2002, 102, 1669.

    Article  CAS  Google Scholar 

  3. L. Antkiewicz-Michaluk, M. Filip, J. Michaluk, I. Romanska, E. Przegalinski, J. Vetulani, J. Neural. Transm., 2007, 114, 307.

    Article  CAS  Google Scholar 

  4. G. Bringmann, A. Irmer, D. Feineis, T. A. M. Gulder, H.-P. Fiedler, Phytochemistry, 2009, 70, 1776.

    Article  CAS  Google Scholar 

  5. T. Wang, L.-G. Zhuo, Z. Li, F. Chen, Z. Ding, Y. He, Q.-H. Fan, J. Xiang, Z.-X. Yu, A. S. C. Chan, J. Am. Chem. Soc., 2011, 133, 9878.

    Article  CAS  Google Scholar 

  6. A. J. Hutf, J. O’Grady, J. Antimicrob. Chemother., 1996, 37, 7.

    Article  Google Scholar 

  7. W.-J. Tang, J. Tan, L.-J. Xu, K.-H. Lam, Q.-H. Fan, A. S. C. Chan, Adv. Synth. Catal., 2010, 352, 1055.

    Article  CAS  Google Scholar 

  8. W. Tang, Y. Sun, L. Xu, T. Wang, Q. Fan, K.-H. Lamc, A. S. C. Chan, Org. Biomol. Chem., 2010, 8, 3464.

    Article  CAS  Google Scholar 

  9. D.-Y. Zhang, D.-S. Wang, M.-C. Wang, C.-B. Yu, K. Gao, Y.-G. Zhou, Synthesis, 2011, 17, 2796.

    Google Scholar 

  10. W.-B. Wang, S.-M. Lu, P.-Y. Yang, X.-W. Han, Y.-G. Zhou, J. Am. Chem. Soc., 2003, 125, 10536.

    Article  CAS  Google Scholar 

  11. L. Xu, K. H. Lam, J. Ji, J. Wu, Q.-H. Fan, W.-H. Loa, A. S. C. Chan, Chem. Commun., 2005, 1390.

    Google Scholar 

  12. S. H. Chan, K. H. Lam, Y.-M. Li, L. Xu, W. Tang, F. L. Lam, W. H. Lo, W. Y. Yu, Q. Fan, A. S. C. Chan, Tetrahedron Asymmetry, 2007, 18, 2625.

    Article  CAS  Google Scholar 

  13. Z.-W. Li, T.-L. Wang, Y.-M. He, Z.-J. Wang, Q.-H. Fan, J. Pan, L.-J. Xu, Org. Lett., 2008, 10, 5265.

    Article  CAS  Google Scholar 

  14. Z.-J. Wang, H.-F. Zhou, T.-L. Wang, Y.-M. He, Q.-H. Fan, Green Chem., 2009, 11, 767.

    Article  CAS  Google Scholar 

  15. C. Li, J. Xiao, J. Am. Chem. Soc., 2008, 130, 13208.

    Article  CAS  Google Scholar 

  16. M. Chang, W. Li, X. Zhang, Angew. Chem., Int. Ed., 2011, 50, 10679.

    Article  CAS  Google Scholar 

  17. M. T. Reetz, X. Li, Chem. Commun., 2006, 2159.

    Google Scholar 

  18. 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 

  19. J.-H. Xie, P.-C. Yan, Q.-Q. Zhang, K.-X. Yuan, Q.-L. Zhou, ACS Catal., 2012, 2, 561.

    Article  CAS  Google Scholar 

  20. M.-W. Chen, Y. Duan, Q.-A. Chen, D.-S. Wang, C.-B. Yu, Y.-G. Zhou, Org. Lett., 2010, 12, 5075.

    Article  CAS  Google Scholar 

  21. Y.-Q. Wang, S.-M. Lu, Y.-G. Zhou, J. Org. Chem., 2007, 72, 3729.

    Article  CAS  Google Scholar 

  22. S. E. Lyubimov, A. A. Tyutyunov, V. N. Kalinin, E. E. Said-Galiev, A. R. Khokhlov, P. V. Petrovskii, V. A. Davankov, Tetrahedron Lett., 2007, 48, 8217.

    Article  CAS  Google Scholar 

  23. S. E. Lyubimov, I. V. Kuchurov, A. A. Tyutyunov, P. V. Petrovskii, V. N. Kalinin, S. G. Zlotin, V. A. Davankov, E. Hey-Hawkins, Catalysis Commun., 2010, 11, 419.

    Article  CAS  Google Scholar 

  24. S. E. Lyubimov, E. A. Rastorguev, P. V. Petrovskii, E. S. Kelbysheva, N. M. Loim, V. A. Davankov, Tetrahedron Lett., 2011, 52, 1395.

    Article  CAS  Google Scholar 

  25. D.-W. Wang, X.-B. Wang, D.-S. Wang, S.-M. Lu, Y.-G. Zhou, Y.-X. Li, J. Org. Chem., 2009, 74, 2780.

    Article  CAS  Google Scholar 

  26. D. Xiao, X. Zhang, Angew. Chem., Int. Ed., 2001, 40, 3425.

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  28. T. V. RajanBabu, T. A. Ayers, G. A. Halliday, K. K. You, J. C. Calabrese, J. Org. Chem., 1997, 62, 6012.

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  30. V. Semeniuchenko, V. Khilya, U. Groth, Synlett, 2009, 20, 271.

    Article  Google Scholar 

  31. T. A. Stephenson, S. M. Morehouse, A. R. Powel, J. P. Heffer, G. Wilkinson, Chem. Commun., 1965, 3632.

    Google Scholar 

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Authors and Affiliations

  1. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    S. E. Lyubimov, E. A. Rastorguev, P. V. Petrovskii & V. A. Davankov

Authors
  1. S. E. Lyubimov
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  2. E. A. Rastorguev
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  3. P. V. Petrovskii
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  4. V. A. Davankov
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Correspondence to S. E. Lyubimov.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2301–2303, December, 2012.

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Lyubimov, S.E., Rastorguev, E.A., Petrovskii, P.V. et al. Asymmetric metal complex hydrogenation of 1-methyl-3,4-dihydroisoquinoline in the presence of amidophosphite ligand. Russ Chem Bull 61, 2322–2325 (2012). https://doi.org/10.1007/s11172-012-0326-9

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  • DOI: https://doi.org/10.1007/s11172-012-0326-9

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