Catalytic (3 + 2) annulation of donor–acceptor aminocyclopropane monoesters and indoles

The efficient catalytic activation of donor–acceptor aminocyclopropanes lacking the commonly used diester acceptor is reported here in a (3 + 2) dearomative annulation with indoles. Bench-stable tosyl-protected aminocyclopropyl esters were converted into cycloadducts in 46–95% yields and up to 95 : ...

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Autores principales: Pirenne, Vincent, Robert, Emma G. L., Waser, Jerome
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8246098/
https://www.ncbi.nlm.nih.gov/pubmed/34257869
http://dx.doi.org/10.1039/d1sc01127h
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author Pirenne, Vincent
Robert, Emma G. L.
Waser, Jerome
author_facet Pirenne, Vincent
Robert, Emma G. L.
Waser, Jerome
author_sort Pirenne, Vincent
collection PubMed
description The efficient catalytic activation of donor–acceptor aminocyclopropanes lacking the commonly used diester acceptor is reported here in a (3 + 2) dearomative annulation with indoles. Bench-stable tosyl-protected aminocyclopropyl esters were converted into cycloadducts in 46–95% yields and up to 95 : 5 diastereomeric ratio using catalytic amounts of triethylsilyl triflimide. Tricyclic indoline frameworks containing four stereogenic centers including all-carbon quaternary centers were obtained.
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spelling pubmed-82460982021-07-12 Catalytic (3 + 2) annulation of donor–acceptor aminocyclopropane monoesters and indoles Pirenne, Vincent Robert, Emma G. L. Waser, Jerome Chem Sci Chemistry The efficient catalytic activation of donor–acceptor aminocyclopropanes lacking the commonly used diester acceptor is reported here in a (3 + 2) dearomative annulation with indoles. Bench-stable tosyl-protected aminocyclopropyl esters were converted into cycloadducts in 46–95% yields and up to 95 : 5 diastereomeric ratio using catalytic amounts of triethylsilyl triflimide. Tricyclic indoline frameworks containing four stereogenic centers including all-carbon quaternary centers were obtained. The Royal Society of Chemistry 2021-05-05 /pmc/articles/PMC8246098/ /pubmed/34257869 http://dx.doi.org/10.1039/d1sc01127h Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Pirenne, Vincent
Robert, Emma G. L.
Waser, Jerome
Catalytic (3 + 2) annulation of donor–acceptor aminocyclopropane monoesters and indoles
title Catalytic (3 + 2) annulation of donor–acceptor aminocyclopropane monoesters and indoles
title_full Catalytic (3 + 2) annulation of donor–acceptor aminocyclopropane monoesters and indoles
title_fullStr Catalytic (3 + 2) annulation of donor–acceptor aminocyclopropane monoesters and indoles
title_full_unstemmed Catalytic (3 + 2) annulation of donor–acceptor aminocyclopropane monoesters and indoles
title_short Catalytic (3 + 2) annulation of donor–acceptor aminocyclopropane monoesters and indoles
title_sort catalytic (3 + 2) annulation of donor–acceptor aminocyclopropane monoesters and indoles
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8246098/
https://www.ncbi.nlm.nih.gov/pubmed/34257869
http://dx.doi.org/10.1039/d1sc01127h
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