Enantioselective Stereodivergent Nucleophile-Dependent Isothiourea-Catalysed Domino Reactions
Anastassia Matviitsuk1, James E Taylor1, David B Cordes1
1EaStCHEM, School of Chemistry, University of St. Andrews, North Haugh, St. Andrews, Fife, KY16 9ST, UK.
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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