Access to Spirooxindole-Fused Cyclopentanes via a Stereoselective Organocascade Reaction Using Bifunctional Catalysis

[Image: see text] The present study reports an asymmetric organocascade reaction of oxindole-derived alkenes with 3-bromo-1-nitropropane efficiently catalyzed by the bifunctional catalyst. Spirooxindole-fused cyclopentanes were produced in moderate-to-good isolated yields (15–69%) with excellent ste...

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Autores principales: Vopálenská, Andrea, Dočekal, Vojtěch, Petrželová, Simona, Císařová, Ivana, Veselý, Jan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10278142/
https://www.ncbi.nlm.nih.gov/pubmed/36705518
http://dx.doi.org/10.1021/acs.joc.2c02478
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author Vopálenská, Andrea
Dočekal, Vojtěch
Petrželová, Simona
Císařová, Ivana
Veselý, Jan
author_facet Vopálenská, Andrea
Dočekal, Vojtěch
Petrželová, Simona
Císařová, Ivana
Veselý, Jan
author_sort Vopálenská, Andrea
collection PubMed
description [Image: see text] The present study reports an asymmetric organocascade reaction of oxindole-derived alkenes with 3-bromo-1-nitropropane efficiently catalyzed by the bifunctional catalyst. Spirooxindole-fused cyclopentanes were produced in moderate-to-good isolated yields (15–69%) with excellent stereochemical outcomes. The synthetic utility of the protocol was exemplified on a set of additional transformations of the corresponding spirooxindole compounds.
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spelling pubmed-102781422023-06-20 Access to Spirooxindole-Fused Cyclopentanes via a Stereoselective Organocascade Reaction Using Bifunctional Catalysis Vopálenská, Andrea Dočekal, Vojtěch Petrželová, Simona Císařová, Ivana Veselý, Jan J Org Chem [Image: see text] The present study reports an asymmetric organocascade reaction of oxindole-derived alkenes with 3-bromo-1-nitropropane efficiently catalyzed by the bifunctional catalyst. Spirooxindole-fused cyclopentanes were produced in moderate-to-good isolated yields (15–69%) with excellent stereochemical outcomes. The synthetic utility of the protocol was exemplified on a set of additional transformations of the corresponding spirooxindole compounds. American Chemical Society 2023-01-27 /pmc/articles/PMC10278142/ /pubmed/36705518 http://dx.doi.org/10.1021/acs.joc.2c02478 Text en © 2023 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 Vopálenská, Andrea
Dočekal, Vojtěch
Petrželová, Simona
Císařová, Ivana
Veselý, Jan
Access to Spirooxindole-Fused Cyclopentanes via a Stereoselective Organocascade Reaction Using Bifunctional Catalysis
title Access to Spirooxindole-Fused Cyclopentanes via a Stereoselective Organocascade Reaction Using Bifunctional Catalysis
title_full Access to Spirooxindole-Fused Cyclopentanes via a Stereoselective Organocascade Reaction Using Bifunctional Catalysis
title_fullStr Access to Spirooxindole-Fused Cyclopentanes via a Stereoselective Organocascade Reaction Using Bifunctional Catalysis
title_full_unstemmed Access to Spirooxindole-Fused Cyclopentanes via a Stereoselective Organocascade Reaction Using Bifunctional Catalysis
title_short Access to Spirooxindole-Fused Cyclopentanes via a Stereoselective Organocascade Reaction Using Bifunctional Catalysis
title_sort access to spirooxindole-fused cyclopentanes via a stereoselective organocascade reaction using bifunctional catalysis
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10278142/
https://www.ncbi.nlm.nih.gov/pubmed/36705518
http://dx.doi.org/10.1021/acs.joc.2c02478
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