Organocatalytic Michael addition-lactonisation of carboxylic acids using α,β-unsaturated trichloromethyl ketones as α,β-unsaturated ester equivalents

Louis C. Morrill, Daniel G. Stark, James E. Taylor, Siobhan R. Smith, James A. Squires, Agathe C.A. D'Hollander, Carmen Simal, Peter Shapland, Timothy J.C. O'Riordan, Andrew D. Smith

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25 Citations (Scopus)

Abstract

Isothiourea HBTM-2.1 catalyses the Michael addition-lactonisation of 2-aryl and 2-alkenylacetic acids and α,β-unsaturated trichloromethyl ketones. Ring-opening of the resulting dihydropyranones and subsequent alcoholysis of the CCl3 ketone with an excess of methanol gives a range of diesters in high diastereo- and enantioselectivity (up to 95:5 dr and >99% ee). Sequential addition of two different nucleophiles to a dihydropyranone gives the corresponding differentially substituted diacid derivative. This journal is

Original languageEnglish
Pages (from-to)9016-9027
Number of pages12
JournalOrganic and Biomolecular Chemistry
Volume12
Issue number44
Early online date6 Oct 2014
DOIs
Publication statusPublished - 28 Nov 2014

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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    Morrill, L. C., Stark, D. G., Taylor, J. E., Smith, S. R., Squires, J. A., D'Hollander, A. C. A., Simal, C., Shapland, P., O'Riordan, T. J. C., & Smith, A. D. (2014). Organocatalytic Michael addition-lactonisation of carboxylic acids using α,β-unsaturated trichloromethyl ketones as α,β-unsaturated ester equivalents. Organic and Biomolecular Chemistry, 12(44), 9016-9027. https://doi.org/10.1039/c4ob01788a