Catalytic Asymmetric Intermolecular [3 + 2] Photocycloaddition of Cyclopropylamines with Electron-Deficient Olefins

An enantioselective intermolecular [3 + 2] cycloaddition of N-arylcyclopropylamines with 2-aryl acrylates/ketones and cyclic ketone-derived terminal olefins via asymmetric photoredox catalysis is reported. A dual catalyst system involving DPZ and a chiral phosphoric acid is effective for the transfo...

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Published in:Organic letters 2023-06, Vol.25 (24), p.4551-4555
Main Authors: Dai, Yating, Huang, Hongchun, Liang, Shuangshuang, Yin, Yanli, Ban, Xu, Zhao, Xiaowei, Jiang, Zhiyong
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cited_by cdi_FETCH-LOGICAL-a345t-612d30defb3de53d15967f36653691767765c331887d06af1f13f6bd83ef43c03
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container_issue 24
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container_title Organic letters
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creator Dai, Yating
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description An enantioselective intermolecular [3 + 2] cycloaddition of N-arylcyclopropylamines with 2-aryl acrylates/ketones and cyclic ketone-derived terminal olefins via asymmetric photoredox catalysis is reported. A dual catalyst system involving DPZ and a chiral phosphoric acid is effective for the transformations, leading to a wide array of valuable cyclopentylamines with high yields, ee’s, and drs. Among them, elaborate modulation of the ester group of 2-aryl acrylates was shown to be effective in improving reactivity, thereby enabling the success of the transformations.
doi_str_mv 10.1021/acs.orglett.3c01585
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title Catalytic Asymmetric Intermolecular [3 + 2] Photocycloaddition of Cyclopropylamines with Electron-Deficient Olefins
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