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Enantioselective stereodivergent nucleophile-dependent isothiourea-catalysed domino reactions

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Author(s)

Anastassia Matviitsuk, James Edward Taylor, David Bradford Cordes, Alexandra Martha Zoya Slawin, Andrew David Smith

School/Research organisations

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.
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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

    Research areas

  • Domino reactions, Enantioselective synthesis, Lewis base, Organocatalysis, α,β-unsaturated acyl ammonium

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