Organocatalytic Michael addition–lactonisation of carboxylic acids using α,β-unsaturated trichloromethyl ketones as α,β-unsaturated ester equivalents
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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.
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 . DOI: 10.1039/c4ob01788a
Organic & Biomolecular Chemistry
© 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
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.
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