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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Detalles Bibliográficos
Autores principales: Wang, Haiyang, Hu, Qingdong, Wang, Mingxu, Guo, Chang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Elsevier 2020
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6995259/
https://www.ncbi.nlm.nih.gov/pubmed/32004992
http://dx.doi.org/10.1016/j.isci.2020.100840
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author Wang, Haiyang
Hu, Qingdong
Wang, Mingxu
Guo, Chang
author_facet Wang, Haiyang
Hu, Qingdong
Wang, Mingxu
Guo, Chang
author_sort Wang, Haiyang
collection PubMed
description 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.
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spelling pubmed-69952592020-02-04 Enantioselective [4+2] Annulation to the Concise Synthesis of Chiral Dihydrocarbazoles Wang, Haiyang Hu, Qingdong Wang, Mingxu Guo, Chang iScience Article 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. Elsevier 2020-01-17 /pmc/articles/PMC6995259/ /pubmed/32004992 http://dx.doi.org/10.1016/j.isci.2020.100840 Text en © 2020 The Author(s) http://creativecommons.org/licenses/by/4.0/ This is an open access article under the CC BY license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Wang, Haiyang
Hu, Qingdong
Wang, Mingxu
Guo, Chang
Enantioselective [4+2] Annulation to the Concise Synthesis of Chiral Dihydrocarbazoles
title Enantioselective [4+2] Annulation to the Concise Synthesis of Chiral Dihydrocarbazoles
title_full Enantioselective [4+2] Annulation to the Concise Synthesis of Chiral Dihydrocarbazoles
title_fullStr Enantioselective [4+2] Annulation to the Concise Synthesis of Chiral Dihydrocarbazoles
title_full_unstemmed Enantioselective [4+2] Annulation to the Concise Synthesis of Chiral Dihydrocarbazoles
title_short Enantioselective [4+2] Annulation to the Concise Synthesis of Chiral Dihydrocarbazoles
title_sort enantioselective [4+2] annulation to the concise synthesis of chiral dihydrocarbazoles
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6995259/
https://www.ncbi.nlm.nih.gov/pubmed/32004992
http://dx.doi.org/10.1016/j.isci.2020.100840
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AT wangmingxu enantioselective42annulationtotheconcisesynthesisofchiraldihydrocarbazoles
AT guochang enantioselective42annulationtotheconcisesynthesisofchiraldihydrocarbazoles

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