Enantioselective synthesis of 3,5,6-substituted dihydropyranones and dihydropyridinones using isothiourea-mediated catalysis
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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.
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 . DOI: 10.1002/asia.201500907
Chemistry-An Asian Journal
Copyright 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
DescriptionWe 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.
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