Enantioselective isothiourea-catalysed trans-dihydropyridinone synthesis using saccharin-derived ketimines : scope and limitations
MetadataShow full item record
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 . https://doi.org/10.1039/C6OB01473A
Organic & Biomolecular Chemistry
Copyright 2016 the Authors. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
DescriptionThe 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.
Items in the St Andrews Research Repository are protected by copyright, with all rights reserved, unless otherwise indicated.