Ring-fused cyclobutanes via cycloisomerization of alkylidenecyclopropane acylsilanes

A novel Lewis acid-catalyzed cycloisomerization of alkylidenecyclopropane acylsilanes is disclosed. The readily available starting materials participate in tandem Prins addition/ring expansion/1,2-silyl shift to grant access to bicyclo[4.2.0]octanes and bicyclo[3.2.0]heptanes, which are common motif...

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Detalles Bibliográficos
Autores principales: Eichenberger, Sarah, Hönig, Moritz, Richter, Matthieu J. R., Gershoni-Poranne, Renana, Carreira, Erick M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8159344/
https://www.ncbi.nlm.nih.gov/pubmed/34122987
http://dx.doi.org/10.1039/d0sc02224a
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author Eichenberger, Sarah
Hönig, Moritz
Richter, Matthieu J. R.
Gershoni-Poranne, Renana
Carreira, Erick M.
author_facet Eichenberger, Sarah
Hönig, Moritz
Richter, Matthieu J. R.
Gershoni-Poranne, Renana
Carreira, Erick M.
author_sort Eichenberger, Sarah
collection PubMed
description A novel Lewis acid-catalyzed cycloisomerization of alkylidenecyclopropane acylsilanes is disclosed. The readily available starting materials participate in tandem Prins addition/ring expansion/1,2-silyl shift to grant access to bicyclo[4.2.0]octanes and bicyclo[3.2.0]heptanes, which are common motifs in terpenoid natural products. Notably, the transformation relies on the ability of acylsilanes to act sequentially as acceptors and donors on the same carbon atom.
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spelling pubmed-81593442021-06-11 Ring-fused cyclobutanes via cycloisomerization of alkylidenecyclopropane acylsilanes Eichenberger, Sarah Hönig, Moritz Richter, Matthieu J. R. Gershoni-Poranne, Renana Carreira, Erick M. Chem Sci Chemistry A novel Lewis acid-catalyzed cycloisomerization of alkylidenecyclopropane acylsilanes is disclosed. The readily available starting materials participate in tandem Prins addition/ring expansion/1,2-silyl shift to grant access to bicyclo[4.2.0]octanes and bicyclo[3.2.0]heptanes, which are common motifs in terpenoid natural products. Notably, the transformation relies on the ability of acylsilanes to act sequentially as acceptors and donors on the same carbon atom. The Royal Society of Chemistry 2020-05-04 /pmc/articles/PMC8159344/ /pubmed/34122987 http://dx.doi.org/10.1039/d0sc02224a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Eichenberger, Sarah
Hönig, Moritz
Richter, Matthieu J. R.
Gershoni-Poranne, Renana
Carreira, Erick M.
Ring-fused cyclobutanes via cycloisomerization of alkylidenecyclopropane acylsilanes
title Ring-fused cyclobutanes via cycloisomerization of alkylidenecyclopropane acylsilanes
title_full Ring-fused cyclobutanes via cycloisomerization of alkylidenecyclopropane acylsilanes
title_fullStr Ring-fused cyclobutanes via cycloisomerization of alkylidenecyclopropane acylsilanes
title_full_unstemmed Ring-fused cyclobutanes via cycloisomerization of alkylidenecyclopropane acylsilanes
title_short Ring-fused cyclobutanes via cycloisomerization of alkylidenecyclopropane acylsilanes
title_sort ring-fused cyclobutanes via cycloisomerization of alkylidenecyclopropane acylsilanes
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8159344/
https://www.ncbi.nlm.nih.gov/pubmed/34122987
http://dx.doi.org/10.1039/d0sc02224a
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AT gershoniporannerenana ringfusedcyclobutanesviacycloisomerizationofalkylidenecyclopropaneacylsilanes
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