Asymmetric Synthesis of 1‑Benzazepine Derivatives via Copper-Catalyzed Intramolecular Reductive Cyclization

Asymmetric Synthesis of 1‑Benzazepine Derivatives via Copper-Catalyzed Intramolecular Reductive Cyclization

An asymmetric construction of enantioenriched 2,3-substituted-1-benzazepine derivatives containing a cyclic tertiary amine moiety was developed by copper-catalyzed reductive intramolecular cyclization of (E)-dienyl arenes with a tethered ketimine. This protocol involves tandem chemo-, regio-, and en...

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Veröffentlicht in:Organic letters 2019-12, Vol.21 (23), p.9699-9703
Hauptverfasser: Li, DingXi, Park, Yeji, Yoon, Woojin, Yun, Hoseop, Yun, Jaesook
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container_issue 23
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container_title Organic letters
container_volume 21
creator Li, DingXi
Park, Yeji
Yoon, Woojin
Yun, Hoseop
Yun, Jaesook
description An asymmetric construction of enantioenriched 2,3-substituted-1-benzazepine derivatives containing a cyclic tertiary amine moiety was developed by copper-catalyzed reductive intramolecular cyclization of (E)-dienyl arenes with a tethered ketimine. This protocol involves tandem chemo-, regio-, and enantioselective hydrocupration and asymmetric cyclization in the presence of a chiral bisphosphine-copper catalyst. Under mild conditions, a broad range of 1-benzazepine derivatives was obtained in good to high yields with high degrees of diastereoselectivity and enantioselectivity.
doi_str_mv 10.1021/acs.orglett.9b03853
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title Asymmetric Synthesis of 1‑Benzazepine Derivatives via Copper-Catalyzed Intramolecular Reductive Cyclization
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