Enantioselective isothiourea-catalysed trans-dihydropyridinone synthesis using saccharin-derived ketimines: scope and limitations
| Autor: | Alexandra M. Z. Slawin, Daniel Graham Stark, Andrew D. Smith, Timothy J. C. O'Riordan, Claire M. Young |
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| Přispěvatelé: | European Commission, University of St Andrews. School of Chemistry, University of St Andrews. Biomedical Sciences Research Complex, University of St Andrews. EaSTCHEM |
| Rok vydání: | 2016 |
| Předmět: |
Dihydropyridines
Stereoisomerism Chemistry Techniques Synthetic 010402 general chemistry 01 natural sciences Biochemistry Catalysis chemistry.chemical_compound Saccharin Nitriles Organic chemistry QD Physical and Theoretical Chemistry 010405 organic chemistry Aryl Organic Chemistry Enantioselective synthesis Thiourea DAS QD Chemistry 0104 chemical sciences chemistry Imines |
| Zdroj: | Organicbiomolecular chemistry. 14(34) |
| ISSN: | 1477-0539 |
| Popis: | 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. 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. Publisher PDF |
| Databáze: | OpenAIRE |
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