Skip to content

Research at St Andrews

Quinidine-Catalysed Enantioselective Synthesis of 6- and 4-Trifluoromethyl-Substituted Dihydropyrans

Research output: Contribution to journalArticle

Abstract

The cinchona alkaloid-catalysed enantioselective formal [4+2] cycloaddition of ethyl 2,3-butadienoate with a range of 1,1,1-trifluoro- and 4,4,4-trifluorobutenones is investigated for the preparation of stereodefined 6- and 4-trifluoromethyl-substituted dihydropyrans. Quinidine proved to be the optimal catalyst, generating the desired products in up to 98 % ee and 81 % yield. Stereo- and chemoselective derivatization of the dihydropyrans through hydrogenation is explored.
Close

Details

Original languageEnglish
JournalEuropean Journal of Organic Chemistry
Volume2016
Issue number21
Early online date23 Jun 2016
DOIs
Publication statusPublished - Jul 2016

    Research areas

  • Organocatalysis, Enantioselective catalysis, Oxygen heterocycles

Discover related content
Find related publications, people, projects and more using interactive charts.

View graph of relations

Related by author

  1. Unanticipated silyl transfer in enantioselective α,β-unsaturated acyl ammonium catalysis using silyl nitronates

    Matviitsuk, A., Greenhalgh, M. D., Taylor, J. E., Nguyen, X. B., Cordes, D. B., Slawin, A. M. Z., Lupton, D. W. & Smith, A. D., 23 Dec 2019, In : Organic Letters. Article ASAP

    Research output: Contribution to journalArticle

  2. Synthesis of fused indoline-cyclobutanone derivatives via an intramolecular [2+2] cycloaddition

    Neyyappadath, R. M., Greenhalgh, M. D., Cordes, D. B., Slawin, A. M. Z. & Smith, A. D., 12 Apr 2019, In : European Journal of Organic Chemistry. Early View

    Research output: Contribution to journalArticle

  3. Chiral AuI- and AuIII-isothiourea complexes: synthesis, characterization and application

    Gasperini, D., Greenhalgh, M., Imad, R., Siddiqui, S., Malik, A., Arshad, F., Choudhary, M. I., Al-Majid, A., Cordes, D., Slawin, A., Nolan, S. & Smith, A. D., 21 Dec 2018, In : Chemistry - A European Journal. Early View

    Research output: Contribution to journalArticle

  4. A C=O•••isothiouronium interaction dictates enantiodiscrimination in acylative kinetic resolution of tertiary heterocyclic alcohols

    Greenhalgh, M. D., Smith, S. M., Walden, D. M., Taylor, J. E., Brice, Z., Robinson, E. R. T., Fallan, C., Cordes, D. B., Slawin, A. M. Z., Richardson, H. C., Grove, M. A., Cheong, P. H-Y. & Smith, A. D., 12 Mar 2018, In : Angewandte Chemie International Edition. 57, 12, p. 3200-3206 7 p.

    Research output: Contribution to journalArticle

Related by journal

  1. Structure‐based design, synthesis and biological evaluation of bis‐tetrahydropyran furan acetogenin mimics targeting the trypanosomatid F1 component of ATP synthase

    Zacharova, M., Tulloch, L., Gould, E., Fraser, A., King, E., Menzies, S., Smith, T. K. & Florence, G. J., 1 Sep 2019, In : European Journal of Organic Chemistry. 2019, 31-32, p. 5434-5440 8 p.

    Research output: Contribution to journalArticle

  2. Synthesis of fused indoline-cyclobutanone derivatives via an intramolecular [2+2] cycloaddition

    Neyyappadath, R. M., Greenhalgh, M. D., Cordes, D. B., Slawin, A. M. Z. & Smith, A. D., 12 Apr 2019, In : European Journal of Organic Chemistry. Early View

    Research output: Contribution to journalArticle

  3. A highly enantioselective alkene methoxycarbonylation enables a concise synthesis of (S)-flurbiprofen

    Harkness, G. J. & Clarke, M. L., 1 Sep 2017, In : European Journal of Organic Chemistry. 2017, 32, p. 4859-4863 5 p.

    Research output: Contribution to journalArticle

ID: 242924163

Top