Skip to content

Research at St Andrews

Isothiourea-catalysed enantioselective Michael addition of N-heterocyclic pronucleophiles to α,β-unsaturated aryl esters

Research output: Contribution to journalArticle

DOI

Open Access permissions

Open

Author(s)

Chang Shu, Honglei Liu, Alexandra Slawin, Cameron L. Carpenter-Warren, Andrew David Smith

School/Research organisations

Abstract

The isothiourea-catalysed enantioselective Michael addition of 3-aryloxindole and 4-substituted-dihydropyrazol-3-one pronucleophiles to α,β-unsaturated p-nitrophenyl esters is reported. This process generates products containing two contiguous stereocentres, one quaternary, in good yields and excellent enantioselectivities (>30 examples, up to > 95 : 5 dr and 99 : 1 er). This protocol harnesses the multifunctional ability of p-nitrophenoxide to promote effective catalysis. In contrast to previous methodologies using tertiary amine Lewis bases, in which the pronucleophile was used as the solvent, this work allows bespoke pronucleophiles to be used in stoichiometric quantities.
Close

Details

Original languageEnglish
Number of pages7
JournalChemical Science
VolumeAdvance Article
Early online date23 Oct 2019
DOIs
Publication statusE-pub ahead of print - 23 Oct 2019

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

View graph of relations

Related by author

  1. Isothiourea-catalyzed atropselective acylation of biaryl phenols via sequential desymmetrization / kinetic resolution

    Munday, E. S., Grove, M., Feoktistova, T., Brueckner, A. C., Walden, D., Young, C. M., Slawin, A. M. Z., Campbell, A., Cheong, P. H-Y. & Smith, A. D., 21 Jan 2020, (Accepted/In press) In : Angewandte Chemie International Edition.

    Research output: Contribution to journalArticle

  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, In : Organic Letters. Article ASAP

    Research output: Contribution to journalArticle

  3. The importance of 1,5-oxygen···chalcogen interactions in enantioselective isochalcogenourea catalysis

    Young, C. M., Elmi, A., Pascoe, D. J., Morris, R. K., McLaughlin, C., Woods, A., Frost, A., De La Houpliere, A., Ling, K. B., Smith, T. K., Slawin, A. M. Z., Willoughby, P. H., Cockroft, S. L. & Smith, A. D., 13 Dec 2019, (Accepted/In press) In : Angewandte Chemie International Edition. In press

    Research output: Contribution to journalArticle

  4. Catalytic enantioselective synthesis of perfluoroalkyl-substituted β-lactones via a concerted asynchronous [2+2] cycloaddition: a synthetic and computational study

    Barrios Antunez, D-J., Greenhalgh, M. D., Brueckner, A. C., Walden, D. M., Elías-Rodríguez, P., Roberts, P., Young, B. G., West, T. H., Slawin, A. M. Z., Cheong, P. H-Y. & Smith, A. D., 28 Jun 2019, In : Chemical Science. 10, 24, p. 6162-6173 12 p.

    Research output: Contribution to journalArticle

Related by journal

  1. A natural solution to photoprotection and isolation of the potent polyene antibiotic, marinomycin A

    Bailey, C. S., Zarins-Tutt, J. S., Agbo, M., Gao, H., Diego-Taboada, A., Gan, M., Hamed Farghal, R. B., Abraham, E., Mackenzie, G., Evans, P. A. & Goss, R. J. M., 28 Aug 2019, In : Chemical Science. 10, 32, p. 7549-7553 5 p.

    Research output: Contribution to journalArticle

  2. Catalytic enantioselective synthesis of perfluoroalkyl-substituted β-lactones via a concerted asynchronous [2+2] cycloaddition: a synthetic and computational study

    Barrios Antunez, D-J., Greenhalgh, M. D., Brueckner, A. C., Walden, D. M., Elías-Rodríguez, P., Roberts, P., Young, B. G., West, T. H., Slawin, A. M. Z., Cheong, P. H-Y. & Smith, A. D., 28 Jun 2019, In : Chemical Science. 10, 24, p. 6162-6173 12 p.

    Research output: Contribution to journalArticle

  3. Hydrocarbon-soluble, hexaanionic fulleride complexes of magnesium

    Lawrence, S., Ohlin, C. A., Cordes, D. B., Slawin, A. M. Z. & Stasch, A., 9 Oct 2019, In : Chemical Science. Advance Article , 10 p.

    Research output: Contribution to journalArticle

  4. Programmable dynamic covalent nanoparticle building blocks with complementary reactivity

    Marro, N., della Sala, F. & Kay, E. R., 14 Nov 2019, In : Chemical Science. Advance Article

    Research output: Contribution to journalArticle

ID: 261991297

Top