title: Enantioselective isothiourea-catalysed trans-dihydropyridinone synthesis using saccharin-derived ketimines: scope and limitations.
abstract: 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.
authors: EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife KY16 9ST, UK. ads10@st-andrews.ac.uk.
authors: Daniel G
authors: DG
authors: Stark
authors: Claire M
authors: CM
authors: Young
authors: Timothy J C
authors: TJ
authors: O'Riordan
authors: Alexandra M Z
authors: AM
authors: Slawin
authors: Andrew D
authors: AD
authors: Smith
mesh_terms: D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D004095:Dihydropyridines / Q000138:chemical synthesis* / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D009570:Nitriles / Q000737:chemistry*; D012439:Saccharin / Q000737:chemistry*; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry*
chemical_list: D004095:Dihydropyridines; D007097:Imines; D009570:Nitriles; C542835:ketimine; C038806:1,4-dihydropyridine; D012439:Saccharin; D013890:Thiourea