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Ion-Tagged Prolinamide Organocatalysts for the Direct Aldol Reaction On-Water

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Abstract

A concise synthesis of two imidazolium ion-tagged prolinamide organocatalysts 3 and 4, varying in anionic component (CF3COO− and PF6 −, respectively) is presented. The latter could be classified as an ionic liquid with a melting point of 66.3 °C, and glass transition temperature of 14.5 °C. The efficiency of each catalyst was compared via a direct aldol reaction revealing a large contrast in catalytic performance, with the catalyst bearing the PF6 − anion being superior. The optimal conditions were determined to be an on-water reaction system, and substrate scoping gave a range of desired aldol products in high conversion (up to >99 %), dr (up to 98:2), and er (up to 96:4). The application of these catalysts to beta-nitrostyrene conjugate addition is also presented.

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Acknowledgments

The authors acknowledge the Institute for Frontier Materials, Strategic Research Centre for Chemistry and Biotechnology, and the Faculty of Science, Engineering, and Built Environment for funding. We acknowledge the Institute for Frontier Materials for the postgraduate scholarship to DE.

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Authors and Affiliations

  1. Institute for Frontier Materials, Carbon Nexus, Deakin University, Pigdons Road, Waurn Ponds Campus, Geelong, VIC, 3216, Australia

    Daniel J. Eyckens, Hannah L. Brozinski, Joshua P. Delaney, Linden Servinis, Sahar Naghashian & Luke C. Henderson

  2. Strategic Research Centre for Chemistry and Biotechnology, Deakin University, Locked Bag 20000, Geelong, VIC, 3220, Australia

    Luke C. Henderson

Authors
  1. Daniel J. Eyckens
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  2. Hannah L. Brozinski
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  3. Joshua P. Delaney
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  4. Linden Servinis
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  5. Sahar Naghashian
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  6. Luke C. Henderson
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Corresponding author

Correspondence to Luke C. Henderson.

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Eyckens, D.J., Brozinski, H.L., Delaney, J.P. et al. Ion-Tagged Prolinamide Organocatalysts for the Direct Aldol Reaction On-Water. Catal Lett 146, 212–219 (2016). https://doi.org/10.1007/s10562-015-1630-4

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  • DOI: https://doi.org/10.1007/s10562-015-1630-4

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