Organocatalytic Michael addition–lactonisation of carboxylic acids using α,β-unsaturated trichloromethyl ketones as α,β-unsaturated ester equivalents
Date
28/11/2014Author
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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 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.
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
Publication
Organic & Biomolecular Chemistry
Status
Peer reviewed
ISSN
1477-0520Type
Journal article
Rights
© Royal Society of Chemistry 2014. This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at http://dx.doi.org/10.1039/C4OB01788A
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.Collections
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