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Copper-catalyzed enantioselective intramolecular alkene amination/intermolecular Heck-type coupling cascade.

ABSTRACT: Enantioselective copper-catalyzed cyclization of ?-alkenylsulfonamides and a ?-alkenylsulfonamide in the presence of a range of vinyl arenes results in variously functionalized 2-substituted chiral nitrogen heterocycles via a formal alkene C-H functionalization process. Application of this reaction to the concise synthesis of a 5-HT(7) receptor antagonist is demonstrated.

SUBMITTER: Liwosz TW

PROVIDER: S-EPMC3314298 | biostudies-literature | 2012 Feb

REPOSITORIES: biostudies-literature

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Copper-catalyzed enantioselective intramolecular alkene amination/intermolecular Heck-type coupling cascade.

Liwosz Timothy W TW Chemler Sherry R SR

Journal of the American Chemical Society 20120124 4

Enantioselective copper-catalyzed cyclization of γ-alkenylsulfonamides and a δ-alkenylsulfonamide in the presence of a range of vinyl arenes results in variously functionalized 2-substituted chiral nitrogen heterocycles via a formal alkene C-H functionalization process. Application of this reaction to the concise synthesis of a 5-HT(7) receptor antagonist is demonstrated. ...[more]

PMID: 22257169

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