Enantioselective synthesis of 3,5,6-substituted dihydropyranones and dihydropyridinones using isothiourea-mediated catalysis
Abstract
The scope of dihydropyranone and dihydropyridinone products accessible by isothiourea-catalysed processes has been expanded and explored through the use of 2-N-tosyliminoacrylates and 2-aroylacrylates in a Michael addition-lactonisation/lactamisation cascade. Notably, in order to ensure reproducibility it is essential to use homoanhydrides as ammonium enolate precursors with 2-aroyl acrylates, while carboxylic acids can be used with 2-N-tosyliminoacrylates, delivering a range of 3,5,6-substituted dihydropyranones and dihydropyridinones with high enantioselectivity (typically >90% ee). The derivatisation of the heterocyclic core of a model 3,5,6-substituted dihydropyranone through hydrogenation is also reported.
Citation
Stark , D G , Morrill , L C , Cordes , D B , Slawin , A M Z , O'Riordan , T J C & Smith , A D 2016 , ' Enantioselective synthesis of 3,5,6-substituted dihydropyranones and dihydropyridinones using isothiourea-mediated catalysis ' , Chemistry-An Asian Journal , vol. 11 , no. 3 , pp. 395–400 . https://doi.org/10.1002/asia.201500907
Publication
Chemistry-An Asian Journal
Status
Peer reviewed
ISSN
1861-4728Type
Journal article
Description
We thank the Royal Society for a University Research Fellowship (ADS), Syngenta and EPSRC grant No. EP/K503162/1 (DGS), and the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007-2013) ERC Grant Agreement No. 279850, for funding.Collections
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