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Catalytic Asymmetric Synthesis of ?-Arylpyrrolidines and Benzo-fused Nitrogen Heterocycles.

ABSTRACT: Herein, we report a practical two-step synthetic route to ?-arylpyrrolidines through Suzuki-Miyaura cross-coupling and enantioselective copper-catalyzed intramolecular hydroamination reactions. The excellent stereoselectivity and broad scope for the transformation of substrates with pharmaceutically relevant heteroarenes render this method a practical and versatile approach for pyrrolidine synthesis. Additionally, this intramolecular hydroamination strategy facilitates the asymmetric synthesis of tetrahydroisoquinolines and medium-ring dibenzo-fused nitrogen heterocycles.

SUBMITTER: Dai XJ

PROVIDER: S-EPMC6553474 | biostudies-literature | 2019 Mar

REPOSITORIES: biostudies-literature

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Catalytic Asymmetric Synthesis of α-Arylpyrrolidines and Benzo-fused Nitrogen Heterocycles.

Dai Xi-Jie XJ Engl Oliver D OD León Thierry T Buchwald Stephen L SL

Angewandte Chemie (International ed. in English) 20190215 11

Herein, we report a practical two-step synthetic route to α-arylpyrrolidines through Suzuki-Miyaura cross-coupling and enantioselective copper-catalyzed intramolecular hydroamination reactions. The excellent stereoselectivity and broad scope for the transformation of substrates with pharmaceutically relevant heteroarenes render this method a practical and versatile approach for pyrrolidine synthesis. Additionally, this intramolecular hydroamination strategy facilitates the asymmetric synthesis o ...[more]

PMID: 30659729

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