Enantioselective Stereodivergent Nucleophile-Dependent Isothiourea-Catalysed Domino Reactions

Anastassia Matviitsuk, James E. Taylor, David B. Cordes, Alexandra M.Z. Slawin, Andrew D. Smith

Research output: Contribution to journalArticlepeer-review

19 Citations (Scopus)

Abstract

α,β-Unsaturated acyl ammoniums generated from the reaction of α,β-unsaturated 2,4,6-trichlorophenol (TCP) esters bearing a pendent enone with an isothiourea organocatalyst are versatile intermediates in a range of enantioselective nucleophile-dependent domino processes to form complex products of diverse topology with excellent stereoselectivity. Use of either 1,3-dicarbonyls, acyl benzothiazoles, or acyl benzimidazoles as nucleophiles allows three distinct, diastereodivergent domino reaction pathways to be accessed to form various fused polycyclic cores containing multiple contiguous stereocentres.

Original languageEnglish
Pages (from-to)17748-17757
Number of pages10
JournalChemistry - A European Journal
Volume22
Issue number49
Early online date11 Oct 2016
DOIs
Publication statusPublished - 5 Dec 2016

Keywords

  • domino reactions
  • enantioselective synthesis
  • Lewis base
  • organocatalysis
  • α,β-unsaturated acyl ammonium

ASJC Scopus subject areas

  • Chemistry(all)

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