Morrill, Louis ORCID: https://orcid.org/0000-0002-6453-7531, 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 |
Official URL: http://dx.doi.org/10.1039/C4OB01788A
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 |
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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: | 28 Oct 2022 09:22 |
URI: | https://orca.cardiff.ac.uk/id/eprint/74290 |
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