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Enantioselective synthesis of 3,5,6-substituted dihydropyranones and dihydropyridinones using isothiourea-mediated catalysis

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Author(s)

Daniel Graham Stark, Louis Christian Morrill, David Bradford Cordes, Alexandra Martha Zoya Slawin, Timothy J.C. O'Riordan, Andrew David Smith

School/Research organisations

Abstract

The scope of dihydropyranone and dihydropyridinone products accessible by isothiourea-catalysed processes has been expanded and explored through the use of 2-N-tosyliminoacrylates and 2-aroylacrylates in a Michael addition-lactonisation/lactamisation cascade. Notably, in order to ensure reproducibility it is essential to use homoanhydrides as ammonium enolate precursors with 2-aroyl acrylates, while carboxylic acids can be used with 2-N-tosyliminoacrylates, delivering a range of 3,5,6-substituted dihydropyranones and dihydropyridinones with high enantioselectivity (typically >90% ee). The derivatisation of the heterocyclic core of a model 3,5,6-substituted dihydropyranone through hydrogenation is also reported.

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Original languageEnglish
Pages (from-to)395–400
Number of pages7
JournalChemistry-An Asian Journal
Volume11
Issue number3
Early online date12 Nov 2015
DOIs
Publication statusPublished - 4 Feb 2016

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