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Organocatalytic Enantioselective α-Bromination of Aldehydes with N-Bromosuccinimide

[Image: see text] Despite the wealth of existing organocatalytic, enantioselective transformations, the α-bromination of aldehydes remains a challenging reaction. The four examples reported to date require expensive, inconvenient brominating agents to achieve the desired products in excellent yields...

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Autores principales: Hutchinson, George, Alamillo-Ferrer, Carla, Fernández-Pascual, Martín, Burés, Jordi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9207931/
https://www.ncbi.nlm.nih.gov/pubmed/35617931
http://dx.doi.org/10.1021/acs.joc.2c00600
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author Hutchinson, George
Alamillo-Ferrer, Carla
Fernández-Pascual, Martín
Burés, Jordi
author_facet Hutchinson, George
Alamillo-Ferrer, Carla
Fernández-Pascual, Martín
Burés, Jordi
author_sort Hutchinson, George
collection PubMed
description [Image: see text] Despite the wealth of existing organocatalytic, enantioselective transformations, the α-bromination of aldehydes remains a challenging reaction. The four examples reported to date require expensive, inconvenient brominating agents to achieve the desired products in excellent yields and enantioselectivities. The preferred brominating agent, N-bromosuccinimide (NBS), has been repeatedly discarded for these reactions because it results in low yields and relatively poor enantioselectivities. We describe a methodology that uses NBS and performs excellently with low catalyst loadings, short reaction times, and mild temperatures.
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spelling pubmed-92079312022-06-21 Organocatalytic Enantioselective α-Bromination of Aldehydes with N-Bromosuccinimide Hutchinson, George Alamillo-Ferrer, Carla Fernández-Pascual, Martín Burés, Jordi J Org Chem [Image: see text] Despite the wealth of existing organocatalytic, enantioselective transformations, the α-bromination of aldehydes remains a challenging reaction. The four examples reported to date require expensive, inconvenient brominating agents to achieve the desired products in excellent yields and enantioselectivities. The preferred brominating agent, N-bromosuccinimide (NBS), has been repeatedly discarded for these reactions because it results in low yields and relatively poor enantioselectivities. We describe a methodology that uses NBS and performs excellently with low catalyst loadings, short reaction times, and mild temperatures. American Chemical Society 2022-05-26 2022-06-17 /pmc/articles/PMC9207931/ /pubmed/35617931 http://dx.doi.org/10.1021/acs.joc.2c00600 Text en © 2022 The Authors. Published by 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 Hutchinson, George
Alamillo-Ferrer, Carla
Fernández-Pascual, Martín
Burés, Jordi
Organocatalytic Enantioselective α-Bromination of Aldehydes with N-Bromosuccinimide
title Organocatalytic Enantioselective α-Bromination of Aldehydes with N-Bromosuccinimide
title_full Organocatalytic Enantioselective α-Bromination of Aldehydes with N-Bromosuccinimide
title_fullStr Organocatalytic Enantioselective α-Bromination of Aldehydes with N-Bromosuccinimide
title_full_unstemmed Organocatalytic Enantioselective α-Bromination of Aldehydes with N-Bromosuccinimide
title_short Organocatalytic Enantioselective α-Bromination of Aldehydes with N-Bromosuccinimide
title_sort organocatalytic enantioselective α-bromination of aldehydes with n-bromosuccinimide
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9207931/
https://www.ncbi.nlm.nih.gov/pubmed/35617931
http://dx.doi.org/10.1021/acs.joc.2c00600
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