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Asymmetric aldol condensation in an ionic liquid-water system catalyzed by (S)-prolinamide derivatives.

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Abstract

Asymmetric aldol reaction of unmodified aldehydes with ketones catalyzed by 1(R),2(R)-bis((S)-prolinamido)cyclohexane (1) or (Rax)-2,2′-bis((S)-prolinamido)-1,1′-binaphtyl (2) proceeds with high yield (68–99%) and diastereoselectivity (dr ≥ 75/25) in the system (1-butyl-3-methylimida-zolium) tetrafluoroborate ([bmim][BF4])-water. The dependence of ee of the dominating anti-diastereomer of aldol on the percentage of water has a maximum at 50 vol.%. Catalyst 1 can be recycled 5 times without losses in the aldol yield, dr and ee.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    A. S. Kucherenko, D. E. Syutkin & S. G. Zlotin

Authors
  1. A. S. Kucherenko
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  2. D. E. Syutkin
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  3. S. G. Zlotin
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Correspondence to A. S. Kucherenko.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 578–581, March, 2008.

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Kucherenko, A.S., Syutkin, D.E. & Zlotin, S.G. Asymmetric aldol condensation in an ionic liquid-water system catalyzed by (S)-prolinamide derivatives.. Russ Chem Bull 57, 591–594 (2008). https://doi.org/10.1007/s11172-008-0092-x

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  • DOI: https://doi.org/10.1007/s11172-008-0092-x

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