Enantioselective isothiourea-catalysed trans-dihydropyridinone synthesis using saccharin-derived ketimines : scope and limitations
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The catalytic enantioselective synthesis of a range of trans-dihydropyridinones from aryl-, heteroaryl- and alkenylacetic acids and saccharin-derived ketimines with good to excellent stereocontrol (15 examples, up to >95:5 dr, up to >99:1 er) is reported. After extensive optimisation, HyperBTM proved the optimal isothiourea catalyst for this transformation at −78 °C, giving trans-dihydropyridones with generally excellent levels of diastereo- and enantioselectivity.
Stark , D G , Young , C M , O'Riordan , T J C , Slawin , A M Z & Smith , A D 2016 , ' Enantioselective isothiourea-catalysed trans -dihydropyridinone synthesis using saccharin-derived ketimines : scope and limitations ' Organic & Biomolecular Chemistry , vol 14 , no. 34 , pp. 8068-8073 . DOI: 10.1039/C6OB01473A
Organic & Biomolecular Chemistry
Copyright 2016 the Authors. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
The authors thank Syngenta and the EPSRC (grant code EP/K503162/1) (DGS) for funding. The European Research Council under the European Union’s Seventh Framework Programme (FP7/2007-2013) ERC Grant Agreement No. 279850 is also acknowledged (CMY). ADS thanks the Royal Society for a Wolfson Research Merit Award. We also thank the EPSRC UK National Mass Spectrometry Facility at Swansea University.
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