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Organocatalytic Michael addition–lactonisation of carboxylic acids using α,β-unsaturated trichloromethyl ketones as α,β-unsaturated ester equivalents
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dc.contributor.author | Morrill, L.C. | |
dc.contributor.author | Stark, D.G. | |
dc.contributor.author | Taylor, J.E. | |
dc.contributor.author | Smith, S.R. | |
dc.contributor.author | Squires, J.A. | |
dc.contributor.author | D'Hollander, A.C.A. | |
dc.contributor.author | Simal Fernandez, Carmen | |
dc.contributor.author | Shapland, P. | |
dc.contributor.author | O'Riordan, T.J.C. | |
dc.contributor.author | Smith, A.D. | |
dc.date.accessioned | 2015-09-22T23:11:47Z | |
dc.date.available | 2015-09-22T23:11:47Z | |
dc.date.issued | 2014-11-28 | |
dc.identifier | 157753969 | |
dc.identifier | 1cf02a60-efac-4cca-ad87-b571a49c017f | |
dc.identifier | 84908377573 | |
dc.identifier | 000344236200025 | |
dc.identifier.citation | Morrill , L C , Stark , D G , Taylor , J E , Smith , S R , Squires , J A , D'Hollander , A C A , Simal Fernandez , 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 & Biomolecular Chemistry , vol. 12 , no. 44 , pp. 9016-9027 . https://doi.org/10.1039/c4ob01788a | en |
dc.identifier.issn | 1477-0520 | |
dc.identifier.other | ORCID: /0000-0002-2104-7313/work/36567506 | |
dc.identifier.uri | https://hdl.handle.net/10023/7527 | |
dc.description | The authors thank the Royal Society for a University Research Fellowship (ADS), The Carnegie Trust for the Universities of Scotland (LCM), Syngenta/EPSRC (Case award to DGS), GSK/EPSRC (CASE award to SRS), the EU (IEF for CS), and the European Research Council under the European Union's Seventh Framework Programme (FP7/2007-2013) ERC Grant Agreement no. 279850 (JET) for funding. | en |
dc.description.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 CCl 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. | |
dc.format.extent | 12 | |
dc.format.extent | 1109060 | |
dc.language.iso | eng | |
dc.relation.ispartof | Organic & Biomolecular Chemistry | en |
dc.subject | QD Chemistry | en |
dc.subject.lcc | QD | en |
dc.title | Organocatalytic Michael addition–lactonisation of carboxylic acids using α,β-unsaturated trichloromethyl ketones as α,β-unsaturated ester equivalents | en |
dc.type | Journal article | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. Biomedical Sciences Research Complex | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.identifier.doi | 10.1039/c4ob01788a | |
dc.description.status | Peer reviewed | en |
dc.date.embargoedUntil | 2015-09-23 |
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