Skip to content

Research at St Andrews

Isothiourea-mediated one-pot synthesis of trifluoromethyl substituted 2-pyrones

Research output: Contribution to journalArticlepeer-review

DOI

Open Access permissions

Open

Author(s)

Pei-Pei Yeh, David S. B. Daniels, David B. Cordes, Alexandra M. Z. Slawin, Andrew D. Smith

School/Research organisations

Abstract

A one-pot isothiourea-mediated Michael addition/lactonization/thiol elimination cascade sequence for the formation of 4,6-disubstituted and 3,4,6-trisubstituted 2-pyrones from (phenylthio)acetic acids and α,β-unsaturated trifluoromethyl ketones is described. The synthesis of a COX-2 inhibitor and the wide-ranging derivatization of the 2-pyrone moiety to trifluoromethyl substituted aromatics and heteroaromatics is also disclosed.

Close

Details

Original languageEnglish
Pages (from-to)964-967
Number of pages4
JournalOrganic Letters
Volume16
Issue number3
Early online date16 Jan 2014
DOIs
Publication statusPublished - 7 Feb 2014

    Research areas

  • Bicyclic-Beta-Lactones, Catalyzed Aldol-Lactonization, Acyl Transfer Catalyst, Asymmetric-Synthesis, Dyotropic Rearrangements, Ncal Reactions, Keto Acids, 3,5-dibromo-2-pyrone

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

View graph of relations

Related by author

  1. Exploring the scope of tandem palladium and isothiourea relay catalysis for the synthesis of α-amino acid derivatives

    Bitai, J., Slawin, A. M. Z., Cordes, D. B. & Smith, A. D., 25 May 2020, In: Molecules. 25, 10, 13 p., 2463.

    Research output: Contribution to journalArticlepeer-review

  2. 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, (E-pub ahead of print) In: Organic Letters. Article ASAP

    Research output: Contribution to journalArticlepeer-review

  3. 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, (E-pub ahead of print) In: European Journal of Organic Chemistry. Early View

    Research output: Contribution to journalArticlepeer-review

  4. 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, (E-pub ahead of print) In: Chemistry - A European Journal. Early View

    Research output: Contribution to journalArticlepeer-review

  5. 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 journalArticlepeer-review

Related by journal

  1. Zelkovamycins B–E, cyclic octapeptides containing rare amino acid residues from an endophytic Kitasatospora sp

    Hao, X., Yu, J., Wang, Y., Connolly, J. A., Liu, Y., Zhang, Y., Yu, L., Cen, S., Goss, R. J. M. & Gan, M., 20 Nov 2020, (E-pub ahead of print) In: Organic Letters. Articles ASAP

    Research output: Contribution to journalArticlepeer-review

  2. Isothiourea-catalyzed enantioselective synthesis of tetrahydro-α-carbolinones

    Liu, H., Slawin, A. M. M. & Smith, A. D., 6 Feb 2020, (E-pub ahead of print) In: Organic Letters. Articles ASAP

    Research output: Contribution to journalArticlepeer-review

  3. 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, (E-pub ahead of print) In: Organic Letters. Article ASAP

    Research output: Contribution to journalArticlepeer-review

  4. Mechanism of Cu-catalyzed aryl boronic acid halode-boronation using electrophilic halogen: development of a base-catalyzed Iododeboronation for radiolabeling applications

    Molloy, J., O’Rourke, K., Frias, C., Sloan, N., West, M., Pimlott, S., Sutherland, A. & Watson, A. J. B., 5 Apr 2019, In: Organic Letters. 21, 7, p. 2488-2492 5 p.

    Research output: Contribution to journalArticlepeer-review

  5. Isothiourea-catalyzed enantioselective functionalization of 2-pyrrolyl acetic acid: two-step synthesis of stereodefined dihydroindolizinones

    Zhang, S., Taylor, J. E., Slawin, A. M. Z. & Smith, A. D., 24 Aug 2018, (E-pub ahead of print) In: Organic Letters. In press

    Research output: Contribution to journalArticlepeer-review

ID: 111957415

Top