Enantioselective Stereodivergent Nucleophile-Dependent Isothiourea-Catalysed Domino Reactions.

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.

SUBMITTER: Matviitsuk A 

PROVIDER: S-EPMC5132085 | biostudies-literature | 2016 Dec

REPOSITORIES: biostudies-literature