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

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, Hype...

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Veröffentlicht in:Organic & biomolecular chemistry 2016-01, Vol.14 (34), p.8068-8073
Hauptverfasser: Stark, Daniel G, Young, Claire M, O'Riordan, Timothy J C, Slawin, Alexandra M Z, Smith, Andrew D
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Chemistry Techniques, Synthetic
Dihydropyridines - chemical synthesis
Dihydropyridines - chemistry
Imines - chemistry
Nitriles - chemistry
Saccharin - chemistry
Stereoisomerism
Thiourea - chemistry
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Zusammenfassung: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c6ob01473a