Enantioselective isothiourea-catalysed trans-dihydropyridinone synthesis using saccharin-derived ketimines : scope and limitations

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.

Citation

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

Publication

Organic & Biomolecular Chemistry

Status

Peer reviewed

DOI

https://doi.org/10.1039/C6OB01473A

ISSN

1477-0520

Type

Journal article

Rights

Description

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.