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

Haiyang Wang; Qingdong Hu; Mingxu Wang; Chang Guo

iScience (Feb 2020)

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

Haiyang Wang,
Qingdong Hu,
Mingxu Wang,
Chang Guo

Affiliations

Haiyang Wang: Hefei National Laboratory for Physical Sciences at the Microscale, University of Science and Technology of China, Hefei 230026, China
Qingdong Hu: Hefei National Laboratory for Physical Sciences at the Microscale, University of Science and Technology of China, Hefei 230026, China
Mingxu Wang: Hefei National Laboratory for Physical Sciences at the Microscale, University of Science and Technology of China, Hefei 230026, China
Chang Guo: Hefei National Laboratory for Physical Sciences at the Microscale, University of Science and Technology of China, Hefei 230026, China; Corresponding author

Journal volume & issue: Vol. 23, no. 2

Abstract

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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. : Catalysis; Organic Synthesis; Organic Reaction Subject Areas: Catalysis, Organic Synthesis, Organic Reaction

Published in iScience

ISSN: 2589-0042 (Online)
Publisher: Elsevier
Country of publisher: United States
LCC subjects: Science
Website: http://www.cell.com/iscience/home

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