Pd-Catalyzed Regioselective Cyclopropanation of 2-Substituted 1,3-Dienes

[Image: see text] A Pd-catalyzed 3,4-regioselective cyclopropanation of 2-substituted 1,3-dienes by decomposition of diazo esters is reported. The vinylcyclopropanes generated are isolated in practical chemical yields with high levels of regioselectivity but low diastereoselectivity. The system oper...

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Autores principales: Kastrati, Agonist, Jaquier, Vincent, Garbo, Michele, Besnard, Céline, Mazet, Clément
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10557126/
https://www.ncbi.nlm.nih.gov/pubmed/37810406
http://dx.doi.org/10.1021/acsorginorgau.3c00024
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author Kastrati, Agonist
Jaquier, Vincent
Garbo, Michele
Besnard, Céline
Mazet, Clément
author_facet Kastrati, Agonist
Jaquier, Vincent
Garbo, Michele
Besnard, Céline
Mazet, Clément
author_sort Kastrati, Agonist
collection PubMed
description [Image: see text] A Pd-catalyzed 3,4-regioselective cyclopropanation of 2-substituted 1,3-dienes by decomposition of diazo esters is reported. The vinylcyclopropanes generated are isolated in practical chemical yields with high levels of regioselectivity but low diastereoselectivity. The system operates under mild reaction conditions, is scalable, and tolerates various sensitive functional groups. A series of original postcatalytic derivatizations is presented to highlight the synthetic potential of the catalytic method.
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spelling pubmed-105571262023-10-07 Pd-Catalyzed Regioselective Cyclopropanation of 2-Substituted 1,3-Dienes Kastrati, Agonist Jaquier, Vincent Garbo, Michele Besnard, Céline Mazet, Clément ACS Org Inorg Au [Image: see text] A Pd-catalyzed 3,4-regioselective cyclopropanation of 2-substituted 1,3-dienes by decomposition of diazo esters is reported. The vinylcyclopropanes generated are isolated in practical chemical yields with high levels of regioselectivity but low diastereoselectivity. The system operates under mild reaction conditions, is scalable, and tolerates various sensitive functional groups. A series of original postcatalytic derivatizations is presented to highlight the synthetic potential of the catalytic method. American Chemical Society 2023-07-25 /pmc/articles/PMC10557126/ /pubmed/37810406 http://dx.doi.org/10.1021/acsorginorgau.3c00024 Text en © 2023 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 Kastrati, Agonist
Jaquier, Vincent
Garbo, Michele
Besnard, Céline
Mazet, Clément
Pd-Catalyzed Regioselective Cyclopropanation of 2-Substituted 1,3-Dienes
title Pd-Catalyzed Regioselective Cyclopropanation of 2-Substituted 1,3-Dienes
title_full Pd-Catalyzed Regioselective Cyclopropanation of 2-Substituted 1,3-Dienes
title_fullStr Pd-Catalyzed Regioselective Cyclopropanation of 2-Substituted 1,3-Dienes
title_full_unstemmed Pd-Catalyzed Regioselective Cyclopropanation of 2-Substituted 1,3-Dienes
title_short Pd-Catalyzed Regioselective Cyclopropanation of 2-Substituted 1,3-Dienes
title_sort pd-catalyzed regioselective cyclopropanation of 2-substituted 1,3-dienes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10557126/
https://www.ncbi.nlm.nih.gov/pubmed/37810406
http://dx.doi.org/10.1021/acsorginorgau.3c00024
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