Enantioselective NHC-catalyzed redox [4+2]-hetero-Diels-Alder reactions using α,β-unsaturated trichloromethyl ketones as amide equivalents

Nassilia Attaba, James Edward Taylor, Alexandra Martha Zoya Slawin, Andrew David Smith

Research output: Contribution to journalArticlepeer-review

26 Citations (Scopus)
2 Downloads (Pure)

Abstract

α,β-Unsaturated trichloromethyl ketones are suitable α,β-unsaturated amide and ester equivalents in N-heterocyclic carbene (NHC)-catalyzed redox hetero-Diels-Alder reactions with azolium enolates generated from α-aroyloxyaldehydes. The initially formed syn-dihydropyranone products can be isolated, or can undergo ring-opening with benzylamine followed by aminolysis of the resulting CCl3 ketone to form a range of diamides with high diastereo- and enantioselectivity (up to >95:5 dr and >99% ee).

Original languageEnglish
Pages (from-to)9728–9739
JournalThe Journal of Organic Chemistry
Volume80
Issue number19
Early online date5 Sept 2015
DOIs
Publication statusPublished - 2 Oct 2015

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