Enantioselective NHC-Catalyzed Redox [4 + 2]-Hetero-Diels-Alder Reactions Using α,β-Unsaturated Trichloromethyl Ketones as Amide Equivalents

Nassilia Attaba, James E. Taylor, Alexandra M.Z. Slawin, Andrew D. Smith

Research output: Contribution to journalArticlepeer-review

25 Citations (Scopus)

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
Number of pages12
JournalJournal of Organic Chemistry
Volume80
Issue number19
Early online date5 Sep 2015
DOIs
Publication statusPublished - 2 Oct 2015

ASJC Scopus subject areas

  • Organic Chemistry

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