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

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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… Click to show full abstract

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.

Keywords: annulation; concise synthesis; synthesis chiral; enantioselective annulation; annulation concise

Journal Title: iScience
Year Published: 2020

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