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Enantioselective Stereodivergent Nucleophile-Dependent Isothiourea-Catalysed Domino Reactions.

ABSTRACT: ?,?-Unsaturated acyl ammoniums generated from the reaction of ?,?-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-other | 2016 Dec

REPOSITORIES: biostudies-other

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Enantioselective Stereodivergent Nucleophile-Dependent Isothiourea-Catalysed Domino Reactions.

Matviitsuk Anastassia A Taylor James E JE Cordes David B DB Slawin Alexandra M Z AM Smith Andrew D AD

Chemistry (Weinheim an der Bergstrasse, Germany) 20161011 49

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 pa ...[more]

PMID: 27727506

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