Jump to main content
Jump to site search

Issue 44, 2014
Previous Article Next Article

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

Author affiliations

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.

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

Back to tab navigation

Supplementary files

Publication details

The article was received on 21 Aug 2014, accepted on 23 Sep 2014 and first published on 06 Oct 2014


Article type: Paper
DOI: 10.1039/C4OB01788A
Citation: Org. Biomol. Chem., 2014,12, 9016-9027
  •   Request permissions

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

    L. C. Morrill, D. G. Stark, J. E. Taylor, S. R. Smith, J. A. Squires, A. C. A. D'Hollander, C. Simal, P. Shapland, T. J. C. O'Riordan and A. D. Smith, Org. Biomol. Chem., 2014, 12, 9016
    DOI: 10.1039/C4OB01788A

Search articles by author

Spotlight

Advertisements