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

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 wit...

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Bibliographic Details
Published iniScience Vol. 23; no. 2; p. 100840
Main Authors Wang, Haiyang, Hu, Qingdong, Wang, Mingxu, Guo, Chang
Format Journal Article
LanguageEnglish
Published United States Elsevier Inc 21.02.2020
Elsevier
Subjects
Catalysis
Organic Reaction
Organic Synthesis
Organic Reaction
Organic Synthesis
Catalysis
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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 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. [Display omitted] •High regio-, chemo-, and enantioselectivity•Broad substrate scope•Dearomatization/aromatization steps proceed under mild conditions•Concise synthesis of chiral analgesic agent Catalysis; Organic Synthesis; Organic Reaction
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ISSN:2589-0042
2589-0042
DOI:10.1016/j.isci.2020.100840