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

Morrill, Louis, Stark, Daniel G., Taylor, James E., Smith, Siobhan R., Squires, James A., D'Hollander, Agathe C. A., Simal, Carmen, Shapland, Peter, O'Riordan, Timothy J. C. and Smith, Andrew D. 2014. Organocatalytic Michael addition–lactonisation of carboxylic acids using α,β-unsaturated trichloromethyl ketones as α,β-unsaturated ester equivalents. Organic & Biomolecular Chemistry 12 (44) , pp. 9016-9027. 10.1039/C4OB01788A

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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.

Item Type: Article
Date Type: Published Online
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Additional Information: First published online 6 October 2014
Publisher: Royal Society of Chemistry
ISSN: 1477-0520
Date of Acceptance: 23 September 2014
Last Modified: 21 Feb 2019 15:48
URI: http://orca.cf.ac.uk/id/eprint/74290

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