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

Timothy W. Liwosz; Sherry R. Chemler

doi:10.1021/ja211272v

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

Timothy W. Liwosz
, Sherry R. Chemler

Chemistry

SUNY Buffalo

Research output: Contribution to journal › Article › peer-review

166 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	2020-2023
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	134
Issue number	4
DOIs	https://doi.org/10.1021/ja211272v
State	Published - Feb 1 2012

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10.1021/ja211272v

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abstract = "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.",

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N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/84856482257

U2 - 10.1021/ja211272v

DO - 10.1021/ja211272v

M3 - Article

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JO - Journal of the American Chemical Society

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ER -

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

Abstract

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