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Asymmetric hydrogenations of diketopiperazines

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Abstract

The dehydrodiketopiperazines 6 undergo face selective hydrogenation with a 5% palladium on carbon catalyst to give the diketopiperazines 7 in high yield with excellent diastereoisomeric ratios (>97%).

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References

  1. H. Poisel and U. Schmidt, Chem. Ber. 106 (1973) 3408.

    CAS  Google Scholar 

  2. T. Kanmera, S. Lee, H. Aoyagi and N. Izumiya, Tetrahedron Lett. 46 (1979) 4483.

    Article  Google Scholar 

  3. N.G. Park, S. Lee, H. Maeda, H. Aoyagi and T. Kato, Bull. Chem. Soc. Jpn. 62 (1989) 2315.

    Article  CAS  Google Scholar 

  4. M. Oba, S. Nakajima and K. Nishiyama, J. Chem. Soc., Chem. Commun. (1996) 1875.

  5. M. Oba, T. Terauchi, Y. Owari, Y. Imai, I. Motoyama and K. Nishiyama, J. Chem. Soc., Perkin Trans. I (1998) 1275.

    Article  Google Scholar 

  6. J.C. Hubbs and C.H. Foster, US Patent 4,992,552 (1991).

  7. K. Tanimura, T. Kato, M. Waki and N. Izumiya, Tetrahedron Lett. 24 (1983) 3737.

    Article  CAS  Google Scholar 

  8. K. Tanimura, T. Kato, M. Waki, S. Lee, Y. Kodera and N. Izumiya, Bull. Chem. Soc. Jpn. 57 (1984) 2193.

    Article  CAS  Google Scholar 

  9. A. Lieberknecht and H. Griesser, Tetrahedron Lett. 28 (1987) 4275.

    Article  CAS  Google Scholar 

  10. S. Takeuchi, Y. Ohgo, N. Miyoshi, C.-gi Shin and Y. Yonezawa, Heterocycles 31 (1990) 2073.

    Article  CAS  Google Scholar 

  11. F. He and B.B. Snider, Synlett (1997) 483.

  12. N. Saito, M.-aki Tanitsu, T. Betsui, R. Suzuki and A. Kubo, Chem. Pharm. Bull. 45 (1997) 1120.

    CAS  Google Scholar 

  13. D.J. Ager, I. Prakash and D.R. Schaad, Chem. Rev. 96 (1996) 835.

    Article  CAS  Google Scholar 

  14. D.J. Ager, R.A. Erickson, D.E. Froen, R.L. Keller, L.M. Klein, R.C. Klix, M.R. Johnson and G. Webber, unpublished results.

  15. U. Schöllkopf, W. Hartwig, K.-H. Pospischil and H. Kehne, Synthesis (1981) 966.

  16. J. Nozulak and U. Schöllkopf, Synthesis (1982) 866.

  17. J.B. Hill, T.-L. Ho, M.R. Johnson, R. Klix, G. Webber and R.A. Erickson, WO 9114378 (1991).

  18. S.D. Bull, S.G. Davies, S.W. Epstein and J.V.A. Quzman, J. Chem. Soc., Chem. Commun. (1998) 659.

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Leeming, P., Fronczek, F.R., Ager, D.J. et al. Asymmetric hydrogenations of diketopiperazines. Topics in Catalysis 13, 175–177 (2000). https://doi.org/10.1023/A:1009001426093

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