Enantioselective [4+2] Annulation to the Concise Synthesis of Chiral Dihydrocarbazoles

Summary: A highly efficient phosphine-catalyzed enantioselective [4 + 2] annulation of allenoates with 3-nitroindoles or 3-nitrobenzothiophenes has been developed. The protocol represents a unique dearomatization–aromatization process to access functionalized dihydrocarbazoles or dihydrodibenzothiop...

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Bibliographic Details
Main Authors: Haiyang Wang, Qingdong Hu, Mingxu Wang, Chang Guo
Format: Article
Language:English
Published: Elsevier 2020-02-01
Series:iScience
Online Access:http://www.sciencedirect.com/science/article/pii/S2589004220300237
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Summary:Summary: A highly efficient phosphine-catalyzed enantioselective [4 + 2] annulation of allenoates with 3-nitroindoles or 3-nitrobenzothiophenes has been developed. The protocol represents a unique dearomatization–aromatization process to access functionalized dihydrocarbazoles or dihydrodibenzothiophenes with high optical purity (up to 97% ee) under mild reaction conditions. The synthetic utility of the highly enantioselective [4 + 2] annulation enables a concise synthesis of analgesic agent. : Catalysis; Organic Synthesis; Organic Reaction Subject Areas: Catalysis, Organic Synthesis, Organic Reaction
ISSN:2589-0042