Dearomative (4 + 3) Cycloaddition Reactions of 3-Alkenylindoles and 3-Alkenylpyrroles to Afford Cyclohepta[b]indoles and Cyclohepta[b]pyrroles

[Image: see text] The dearomative (4 + 3) cycloaddition reactions of 3-alkenylindoles with in situ-generated oxyallyl cations furnish cyclohepta[b]indoles, functionality-rich frameworks found in many bioactive compounds, including all pentacyclic ambiguine alkaloids. The analogous reactions between...

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Autores principales: Taenzler, Ferdinand, Xu, Jiasu, Athe, Sudhakar, Rawal, Viresh H.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9664489/
https://www.ncbi.nlm.nih.gov/pubmed/36315976
http://dx.doi.org/10.1021/acs.orglett.2c02983
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author Taenzler, Ferdinand
Xu, Jiasu
Athe, Sudhakar
Rawal, Viresh H.
author_facet Taenzler, Ferdinand
Xu, Jiasu
Athe, Sudhakar
Rawal, Viresh H.
author_sort Taenzler, Ferdinand
collection PubMed
description [Image: see text] The dearomative (4 + 3) cycloaddition reactions of 3-alkenylindoles with in situ-generated oxyallyl cations furnish cyclohepta[b]indoles, functionality-rich frameworks found in many bioactive compounds, including all pentacyclic ambiguine alkaloids. The analogous reactions between oxyallyl cations and 3-alkenylpyrroles afford cyclohepta[b]pyrroles. The cycloadducts are generally formed in good to high yields and diastereoselectivities and can be readily transformed into useful derivatives. Additionally, we report preliminary investigations into the enantioselective catalysis of the dearomative (4 + 3) cycloaddition using imidodiphosphorimidate catalysts.
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spelling pubmed-96644892022-11-15 Dearomative (4 + 3) Cycloaddition Reactions of 3-Alkenylindoles and 3-Alkenylpyrroles to Afford Cyclohepta[b]indoles and Cyclohepta[b]pyrroles Taenzler, Ferdinand Xu, Jiasu Athe, Sudhakar Rawal, Viresh H. Org Lett [Image: see text] The dearomative (4 + 3) cycloaddition reactions of 3-alkenylindoles with in situ-generated oxyallyl cations furnish cyclohepta[b]indoles, functionality-rich frameworks found in many bioactive compounds, including all pentacyclic ambiguine alkaloids. The analogous reactions between oxyallyl cations and 3-alkenylpyrroles afford cyclohepta[b]pyrroles. The cycloadducts are generally formed in good to high yields and diastereoselectivities and can be readily transformed into useful derivatives. Additionally, we report preliminary investigations into the enantioselective catalysis of the dearomative (4 + 3) cycloaddition using imidodiphosphorimidate catalysts. American Chemical Society 2022-10-31 2022-11-11 /pmc/articles/PMC9664489/ /pubmed/36315976 http://dx.doi.org/10.1021/acs.orglett.2c02983 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Taenzler, Ferdinand
Xu, Jiasu
Athe, Sudhakar
Rawal, Viresh H.
Dearomative (4 + 3) Cycloaddition Reactions of 3-Alkenylindoles and 3-Alkenylpyrroles to Afford Cyclohepta[b]indoles and Cyclohepta[b]pyrroles
title Dearomative (4 + 3) Cycloaddition Reactions of 3-Alkenylindoles and 3-Alkenylpyrroles to Afford Cyclohepta[b]indoles and Cyclohepta[b]pyrroles
title_full Dearomative (4 + 3) Cycloaddition Reactions of 3-Alkenylindoles and 3-Alkenylpyrroles to Afford Cyclohepta[b]indoles and Cyclohepta[b]pyrroles
title_fullStr Dearomative (4 + 3) Cycloaddition Reactions of 3-Alkenylindoles and 3-Alkenylpyrroles to Afford Cyclohepta[b]indoles and Cyclohepta[b]pyrroles
title_full_unstemmed Dearomative (4 + 3) Cycloaddition Reactions of 3-Alkenylindoles and 3-Alkenylpyrroles to Afford Cyclohepta[b]indoles and Cyclohepta[b]pyrroles
title_short Dearomative (4 + 3) Cycloaddition Reactions of 3-Alkenylindoles and 3-Alkenylpyrroles to Afford Cyclohepta[b]indoles and Cyclohepta[b]pyrroles
title_sort dearomative (4 + 3) cycloaddition reactions of 3-alkenylindoles and 3-alkenylpyrroles to afford cyclohepta[b]indoles and cyclohepta[b]pyrroles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9664489/
https://www.ncbi.nlm.nih.gov/pubmed/36315976
http://dx.doi.org/10.1021/acs.orglett.2c02983
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