Base-Promoted Intramolecular Addition of Vinyl Cyclopropanecarboxamides to Access Conformationally Restricted Aza[3.1.0]bicycles

3-Azabicyclo[3.1.0]hexanes are common structural components in natural products and bioactive compounds. Traditionally, the metal-mediated cyclopropanation domino reaction of chain enzymes is the most commonly used strategy for the construction of this type of aza[3.1.0]bicycle derivative. In this s...

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Autores principales: Li, Jingya, Zhang, Zhiguo, Chen, Liming, Li, Mengjuan, Zhang, Xingjie, Zhang, Guisheng
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10179847/
https://www.ncbi.nlm.nih.gov/pubmed/37175101
http://dx.doi.org/10.3390/molecules28093691
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author Li, Jingya
Zhang, Zhiguo
Chen, Liming
Li, Mengjuan
Zhang, Xingjie
Zhang, Guisheng
author_facet Li, Jingya
Zhang, Zhiguo
Chen, Liming
Li, Mengjuan
Zhang, Xingjie
Zhang, Guisheng
author_sort Li, Jingya
collection PubMed
description 3-Azabicyclo[3.1.0]hexanes are common structural components in natural products and bioactive compounds. Traditionally, the metal-mediated cyclopropanation domino reaction of chain enzymes is the most commonly used strategy for the construction of this type of aza[3.1.0]bicycle derivative. In this study, a base-promoted intramolecular addition of alkenes used to deliver conformationally restricted highly substituted aza[3.1.0]bicycles is reported. This reaction was tailor-made for saturated aza[3.1.0] bicycle-containing fused bicyclic compounds that may be applied in the development of concise and divergent total syntheses of bioactive compounds.
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spelling pubmed-101798472023-05-13 Base-Promoted Intramolecular Addition of Vinyl Cyclopropanecarboxamides to Access Conformationally Restricted Aza[3.1.0]bicycles Li, Jingya Zhang, Zhiguo Chen, Liming Li, Mengjuan Zhang, Xingjie Zhang, Guisheng Molecules Article 3-Azabicyclo[3.1.0]hexanes are common structural components in natural products and bioactive compounds. Traditionally, the metal-mediated cyclopropanation domino reaction of chain enzymes is the most commonly used strategy for the construction of this type of aza[3.1.0]bicycle derivative. In this study, a base-promoted intramolecular addition of alkenes used to deliver conformationally restricted highly substituted aza[3.1.0]bicycles is reported. This reaction was tailor-made for saturated aza[3.1.0] bicycle-containing fused bicyclic compounds that may be applied in the development of concise and divergent total syntheses of bioactive compounds. MDPI 2023-04-25 /pmc/articles/PMC10179847/ /pubmed/37175101 http://dx.doi.org/10.3390/molecules28093691 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Li, Jingya
Zhang, Zhiguo
Chen, Liming
Li, Mengjuan
Zhang, Xingjie
Zhang, Guisheng
Base-Promoted Intramolecular Addition of Vinyl Cyclopropanecarboxamides to Access Conformationally Restricted Aza[3.1.0]bicycles
title Base-Promoted Intramolecular Addition of Vinyl Cyclopropanecarboxamides to Access Conformationally Restricted Aza[3.1.0]bicycles
title_full Base-Promoted Intramolecular Addition of Vinyl Cyclopropanecarboxamides to Access Conformationally Restricted Aza[3.1.0]bicycles
title_fullStr Base-Promoted Intramolecular Addition of Vinyl Cyclopropanecarboxamides to Access Conformationally Restricted Aza[3.1.0]bicycles
title_full_unstemmed Base-Promoted Intramolecular Addition of Vinyl Cyclopropanecarboxamides to Access Conformationally Restricted Aza[3.1.0]bicycles
title_short Base-Promoted Intramolecular Addition of Vinyl Cyclopropanecarboxamides to Access Conformationally Restricted Aza[3.1.0]bicycles
title_sort base-promoted intramolecular addition of vinyl cyclopropanecarboxamides to access conformationally restricted aza[3.1.0]bicycles
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10179847/
https://www.ncbi.nlm.nih.gov/pubmed/37175101
http://dx.doi.org/10.3390/molecules28093691
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