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

Daniel Graham Stark, Claire Mary Young, Timothy J C O'Riordan, Alexandra Martha Zoya Slawin, Andrew David Smith

Research output: Contribution to journalArticlepeer-review

18 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)8068-8073
Number of pages6
JournalOrganic & Biomolecular Chemistry
Volume14
Issue number34
Early online date26 Jul 2016
DOIs
Publication statusPublished - 14 Sept 2016

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