Metal-Free Regiodivergent Addition of Carbon Nucleophiles to α,β-Unsaturated Electrophiles

A mild and metal-free regiodivergent addition of carbon nucleophiles to α,β-unsaturated electrophiles was developed. Total 1,2-regioselectivity was observed in the addition of nitrobenzyl chloride derivative 1 to α,β-unsaturated aldehydes 2 in the presence of TDAE. Moreover, the reaction between p-n...

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Autores principales: Spitz, Cédric, Giuglio-Tonolo, Alain G., Terme, Thierry, Vanelle, Patrice
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2017
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6152382/
https://www.ncbi.nlm.nih.gov/pubmed/28708088
http://dx.doi.org/10.3390/molecules22071178
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author Spitz, Cédric
Giuglio-Tonolo, Alain G.
Terme, Thierry
Vanelle, Patrice
author_facet Spitz, Cédric
Giuglio-Tonolo, Alain G.
Terme, Thierry
Vanelle, Patrice
author_sort Spitz, Cédric
collection PubMed
description A mild and metal-free regiodivergent addition of carbon nucleophiles to α,β-unsaturated electrophiles was developed. Total 1,2-regioselectivity was observed in the addition of nitrobenzyl chloride derivative 1 to α,β-unsaturated aldehydes 2 in the presence of TDAE. Moreover, the reaction between p-nitrobenzyl chloride 1a and α,β-unsaturated iminium salts 4 led to the formation of the 1,4-adduct with total regioselectivity.
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spelling pubmed-61523822018-11-13 Metal-Free Regiodivergent Addition of Carbon Nucleophiles to α,β-Unsaturated Electrophiles Spitz, Cédric Giuglio-Tonolo, Alain G. Terme, Thierry Vanelle, Patrice Molecules Article A mild and metal-free regiodivergent addition of carbon nucleophiles to α,β-unsaturated electrophiles was developed. Total 1,2-regioselectivity was observed in the addition of nitrobenzyl chloride derivative 1 to α,β-unsaturated aldehydes 2 in the presence of TDAE. Moreover, the reaction between p-nitrobenzyl chloride 1a and α,β-unsaturated iminium salts 4 led to the formation of the 1,4-adduct with total regioselectivity. MDPI 2017-07-14 /pmc/articles/PMC6152382/ /pubmed/28708088 http://dx.doi.org/10.3390/molecules22071178 Text en © 2017 by the authors. 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 (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Spitz, Cédric
Giuglio-Tonolo, Alain G.
Terme, Thierry
Vanelle, Patrice
Metal-Free Regiodivergent Addition of Carbon Nucleophiles to α,β-Unsaturated Electrophiles
title Metal-Free Regiodivergent Addition of Carbon Nucleophiles to α,β-Unsaturated Electrophiles
title_full Metal-Free Regiodivergent Addition of Carbon Nucleophiles to α,β-Unsaturated Electrophiles
title_fullStr Metal-Free Regiodivergent Addition of Carbon Nucleophiles to α,β-Unsaturated Electrophiles
title_full_unstemmed Metal-Free Regiodivergent Addition of Carbon Nucleophiles to α,β-Unsaturated Electrophiles
title_short Metal-Free Regiodivergent Addition of Carbon Nucleophiles to α,β-Unsaturated Electrophiles
title_sort metal-free regiodivergent addition of carbon nucleophiles to α,β-unsaturated electrophiles
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6152382/
https://www.ncbi.nlm.nih.gov/pubmed/28708088
http://dx.doi.org/10.3390/molecules22071178
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