Skip to content

Research at St Andrews

6-exo-trig Michael addition-lactonizations for catalytic enantioselective chromenone synthesis

Research output: Contribution to journalArticle

DOI

Open Access permissions

Open

Abstract

The catalytic enantioselective 6-exo-trig Michael addition-lactonization of enone-acid substrates to form cis-chromenones with high diastereo- and enantiocontrol was developed using the commercially available isothiourea tetramisole. An acidic workup proved necessary to minimize product epimerization and maximize product er, providing cis-chromenones in excellent yield, and with excellent diastereo- and enantioselectivity.
Close

Details

Original languageEnglish
Pages (from-to)2555-2558
JournalChemical Communications
Volume53
Issue number17
Early online date19 Jan 2017
DOIs
Publication statusPublished - 28 Feb 2017

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. Chemical Communications (Journal)

    Nigel Peter Botting (Editor)
    2005 → …

    Activity: Publication peer-review and editorial work typesEditor of research journal

Related by journal

  1. Unprecedented tin iodide perovskite-like structures featuring ordering of organic moieties

    McNulty, J. A. & Lightfoot, P., 28 Apr 2020, In : Chemical Communications. 56, 33, p. 4543-4546

    Research output: Contribution to journalArticle

  2. Buchwald Hartwig diversification of unprotected halotryptophans, halotryptophan containing tripeptides and the natural product barettin in aqueous conditions

    Renault, Y. J. G., Lynch, R., Marelli, E., Sharma, S. V., Pubill Ulldemolins, C., Sharp, J., Cartmell, C., Cárdenas, P. & Goss, R. J. M., 8 Oct 2019, In : Chemical Communications. Advance Article, 4 p.

    Research output: Contribution to journalReview article

  3. Continuous flow knitting of a triptycene hypercrosslinked polymer

    Lau, C. H., Lu, T., Sun, S-P., Chen, X., Carta, M. & Dawson, D. M., 28 Jul 2019, In : Chemical Communications. 55, 59, p. 8571-8574 4 p.

    Research output: Contribution to journalArticle

  4. Cu-NHC azide complex: synthesis and reactivity

    Trose, M., Nahra, F., Cordes, D. B., Slawin, A. M. Z. & Cazin, C., 14 Oct 2019, In : Chemical Communications. 55, 80, p. 12068-12071

    Research output: Contribution to journalArticle

ID: 248996963

Top