Russian Chemical Bulletin

, Volume 58, Issue 9, pp 1899–1902 | Cite as

Enantioselective synthesis of β-hydroxy ketones from heterocyclic aldehydes in water catalyzed by a recyclable organocatalyst bearing an ionic liquid moiety

  • D. E. Siyutkin
  • A. S. Kucherenko
  • S. G. Zlotin
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Abstract

The aldol reactions of cyclic (heterocyclic) ketones and heterocyclic aldehydes catalyzed by (4R,S)-4-hydroxyproline modified with a ionic liquid moiety proceed with high yields and diastereo- and enantioselectivity in the presence of water. The catalyst retained its activity and selectivity for at least five cycles.

Key words

organocatalysis asymmetric aldol reaction water β-hydroxy ketones heterocyclic aldehydes catalyst regeneration ionic liquids 
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References

  1. 1.(a)
    Y. Kamano, H. Zhang, Y. Ichihara, H. Kizu, K. Komiyama, G. R. Pettit, Tetrahedron Lett., 1995, 36, 2783; (b) S. Ogawa, N. Shibata, J. Inagaki, S. Nakamura, T. Toru, M. Shiro, Angew. Chem. Int. Ed., 2007, 46, 8666; (c) D. M. Mans, W. H. Pearson, Org. Lett., 2004, 6, 3305; (d) D. E. Ward, V. Jheengut, G. E. Beye, J. Org. Chem., 2006, 71, 8989.CrossRefGoogle Scholar
  2. 2.(a)
    B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395; (b) W. Notz, B. List, J. Am. Chem. Soc., 2000, 122, 7386; (c) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas III, J. Am. Chem. Soc., 2001, 123, 5260.CrossRefGoogle Scholar
  3. 3.(a)
    A. Berkessel, Asymmetric Organocatalysis, WILEY-VCH, Verlag GmbH and Co. KGaA, Weinheim, 2005, 435 p.; (b) Enantioselective Organocatalysis (Ed. P. I. Dalko), Wiley-VCH, Verlag GmbH & Co. KGaA, 2007, 536 p.; (c) S. Mukherjee, J. W. Yang, S. Hoffman, B. List, Chem. Rev., 2007, 107, 5471.CrossRefGoogle Scholar
  4. 4.(a)
    J.-R. Chen, H.-H. Lu, X.-Y. Li, L. Cheng, J. Wan, W.-J. Xiao, Org. Lett., 2005, 7, 4543; (b) A. Russo, G. Botta, A. Lattanzi, Tetrahedron, 2007, 63, 11886; (c) A. S. Kucherenko, D. E. Siyutkin, S. G. Zlotin, Izv. Akad. Nauk, Ser. Khim., 2008, 578 [Russ. Chem. Bull., Int Ed., 2008, 57, 591].CrossRefGoogle Scholar
  5. 5.(a)
    V. Maya, M. Raj, V. K. Singh, Org. Lett., 2007, 9, 2593; (b) M. Lei, L. Shi, G. Li, S. Chen, W. Fang, Z. Ge, T. Cheng, R. Li, Tetrahedron, 2007, 63, 7892.CrossRefGoogle Scholar
  6. 6.(a)
    Y. Wu, Y. Zhang, M. Yu, G. Zhao, S. Wang, Org. Lett., 2006, 8, 4417; (b) D. Font, C. Jimeno, M. A. Pericas, Org. Lett., 2006, 8, 4653; (c) D. Font, S. Sayalero, A. Bastero, C. Jimeno, M. A. Pericas, Org. Lett., 2008, 10, 337; (d) M. Gruttadauria, F. Giacalone, A. M. Marculescu, P. L. Meo, S. Riela, R. Noto, Eur. J. Org. Chem., 2007, 4688.CrossRefGoogle Scholar
  7. 7.(a)
    D. E. Siyutkin, A. S. Kucherenko, M. I. Struchkova, S. G. Zlotin, Tetrahedron Lett., 2008, 49, 1212; (b) D. E. Siyutkin, A. S. Kucherenko, S. G. Zlotin, Tetrahedron, 2009, 65, 1366.CrossRefGoogle Scholar
  8. 8.
    M. D. Mashkovskii, Lekarstvennye sredstva [Medical Products], 2 Vols, OOO Novaya Volna, Moscow, 2002 (in Russian).Google Scholar
  9. 9.
    M. Lombardo, S. Easwar, F. Pasi, C. Trombini, D. D. Dhavale, Tetarhedron, 2008, 64, 9203.CrossRefGoogle Scholar
  10. 10.
    Y. Hayashi, T. Sumiya, J. Takahashi, H. Gotoh, T. Urushima, M. Shoji, Angew. Chem. Int. Ed., 2006, 45, 958.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, Inc.  2009

Authors and Affiliations

  • D. E. Siyutkin
    • 1
  • A. S. Kucherenko
    • 1
  • S. G. Zlotin
    • 1
  1. 1.N. D. Zelinsky of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

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