Diastereoselective ring opening of fully-substituted cyclopropanes via intramolecular Friedel–Crafts alkylation

We herein disclose a diastereoselective ring opening of non-donor–acceptor cyclopropanes via an intramolecular Friedel–Crafts alkylation en route to functionalized dihydronaphthalene scaffolds possessing quaternary carbon stereocentres. The transformation proceeds through a selective bond breaking a...

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Autores principales: Lanke, Veeranjaneyulu, Zhang, Fa-Guang, Kaushansky, Alexander, Marek, Ilan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6979362/
https://www.ncbi.nlm.nih.gov/pubmed/32055326
http://dx.doi.org/10.1039/c9sc03832a
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author Lanke, Veeranjaneyulu
Zhang, Fa-Guang
Kaushansky, Alexander
Marek, Ilan
author_facet Lanke, Veeranjaneyulu
Zhang, Fa-Guang
Kaushansky, Alexander
Marek, Ilan
author_sort Lanke, Veeranjaneyulu
collection PubMed
description We herein disclose a diastereoselective ring opening of non-donor–acceptor cyclopropanes via an intramolecular Friedel–Crafts alkylation en route to functionalized dihydronaphthalene scaffolds possessing quaternary carbon stereocentres. The transformation proceeds through a selective bond breaking at the most alkylated carbon centre with a pure retention of configuration. Mechanistic investigations and computational studies revealed that alkoxy functionality is the key for selective bond breaking leading to a complete retention of configuration.
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spelling pubmed-69793622020-02-13 Diastereoselective ring opening of fully-substituted cyclopropanes via intramolecular Friedel–Crafts alkylation Lanke, Veeranjaneyulu Zhang, Fa-Guang Kaushansky, Alexander Marek, Ilan Chem Sci Chemistry We herein disclose a diastereoselective ring opening of non-donor–acceptor cyclopropanes via an intramolecular Friedel–Crafts alkylation en route to functionalized dihydronaphthalene scaffolds possessing quaternary carbon stereocentres. The transformation proceeds through a selective bond breaking at the most alkylated carbon centre with a pure retention of configuration. Mechanistic investigations and computational studies revealed that alkoxy functionality is the key for selective bond breaking leading to a complete retention of configuration. Royal Society of Chemistry 2019-08-27 /pmc/articles/PMC6979362/ /pubmed/32055326 http://dx.doi.org/10.1039/c9sc03832a Text en This journal is © The Royal Society of Chemistry 2019 http://creativecommons.org/licenses/by-nc/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0)
spellingShingle Chemistry
Lanke, Veeranjaneyulu
Zhang, Fa-Guang
Kaushansky, Alexander
Marek, Ilan
Diastereoselective ring opening of fully-substituted cyclopropanes via intramolecular Friedel–Crafts alkylation
title Diastereoselective ring opening of fully-substituted cyclopropanes via intramolecular Friedel–Crafts alkylation
title_full Diastereoselective ring opening of fully-substituted cyclopropanes via intramolecular Friedel–Crafts alkylation
title_fullStr Diastereoselective ring opening of fully-substituted cyclopropanes via intramolecular Friedel–Crafts alkylation
title_full_unstemmed Diastereoselective ring opening of fully-substituted cyclopropanes via intramolecular Friedel–Crafts alkylation
title_short Diastereoselective ring opening of fully-substituted cyclopropanes via intramolecular Friedel–Crafts alkylation
title_sort diastereoselective ring opening of fully-substituted cyclopropanes via intramolecular friedel–crafts alkylation
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6979362/
https://www.ncbi.nlm.nih.gov/pubmed/32055326
http://dx.doi.org/10.1039/c9sc03832a
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AT zhangfaguang diastereoselectiveringopeningoffullysubstitutedcyclopropanesviaintramolecularfriedelcraftsalkylation
AT kaushanskyalexander diastereoselectiveringopeningoffullysubstitutedcyclopropanesviaintramolecularfriedelcraftsalkylation
AT marekilan diastereoselectiveringopeningoffullysubstitutedcyclopropanesviaintramolecularfriedelcraftsalkylation

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