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Application of hydroxyproline derivatives in enantioselective α-amination reactions in organic and aqueous environments: a structure-activity relationship study

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Abstract

We examined the activity of a series of L-hydroxyproline derivatives in enantioselective α-amination reaction between diethyl azodicarboxylate and propanal both in organic and aqueous media. In organic media most of the catalysts showed high activity and enantioselectivities comparable to that accessible with L-proline that is among the best catalysts in the reaction. The catalysts showed good activity under aqueous conditions as well; however, only low enantioselectivities were obtained in this case, primarily due to the racemisation of the product under the reaction conditions. Thus, the attempted achiral acid/base additive-driven stereocontrol was not feasible on a practical level.

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Acknowledgments

Financial support from the National Research, Development and Innovation Office, Hungary (OTKA Grants K 109278 and PD 115436), is gratefully acknowledged. Z. Szécsényi (Institute of Pharmaceutical Chemistry, University of Szeged) is acknowledged for technical support. M. S. was supported by a Magyary Zoltán fellowship within the framework of TÁMOP 4.2.4. A/2-11-1-2012-0001 (A2-MZPD-12-0139) and he is currently János Bolyai Research Scholar of the Hungarian Academy of Sciences (BO/00113/15/7). G. L. acknowledges the János Bolyai Research Scholarship from the Hungarian Academy of Sciences. We thank the anonymous reviewers for their insightful comments, which improved the quality of the manuscript.

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Author notes

  1. Gábor London

    Present address: Institute of Organic Chemistry, Research Centre for Natural Sciences, Hungarian Academy of Sciences, Magyar tudósok körútja 2, Budapest, 1117, Hungary

Authors and Affiliations

  1. Department of Organic Chemistry, University of Szeged, Dóm tér 8, Szeged, H-6720, Hungary

    András A. Gurka & Mihály Bartók

  2. MTA-SZTE Stereochemistry Research Group, Dóm tér 8, Szeged, H-6720, Hungary

    Kornél Szőri, Mihály Bartók & Gábor London

  3. Institute of Chemistry, University of Miskolc, Miskolc-Egyetemváros, A/2., A-3, Miskolc, H-3515, Hungary

    Milán Szőri

Authors
  1. András A. Gurka
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  2. Kornél Szőri
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  4. Mihály Bartók
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Correspondence to Mihály Bartók or Gábor London.

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Gurka, A.A., Szőri, K., Szőri, M. et al. Application of hydroxyproline derivatives in enantioselective α-amination reactions in organic and aqueous environments: a structure-activity relationship study. Struct Chem 28, 415–421 (2017). https://doi.org/10.1007/s11224-016-0873-z

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  • DOI: https://doi.org/10.1007/s11224-016-0873-z

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