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

ABSTRACT: 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.

SUBMITTER: Wang H

PROVIDER: S-EPMC6995259 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature

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

Wang Haiyang H Hu Qingdong Q Wang Mingxu M Guo Chang C

iScience 20200117 2

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. ...[more]

PMID: 32004992

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