Asymmetric C–H functionalization of cyclopropanes using an isoleucine-NH(2) bidentate directing group

The systematic investigation of substrate-bound α-amino acid auxiliaries has resulted in catalytic asymmetric C–H functionalization of cyclopropanes enabled by amino acid amides as chiral bidentate directing groups. The use of an Ile-NH(2) auxiliary embedded in the substrate provided excellent level...

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Detalles Bibliográficos
Autores principales: Kim, Jinhee, Sim, Mikyung, Kim, Namhoon, Hong, Sungwoo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2015
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5659170/
https://www.ncbi.nlm.nih.gov/pubmed/29511524
http://dx.doi.org/10.1039/c5sc01137j
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author Kim, Jinhee
Sim, Mikyung
Kim, Namhoon
Hong, Sungwoo
author_facet Kim, Jinhee
Sim, Mikyung
Kim, Namhoon
Hong, Sungwoo
author_sort Kim, Jinhee
collection PubMed
description The systematic investigation of substrate-bound α-amino acid auxiliaries has resulted in catalytic asymmetric C–H functionalization of cyclopropanes enabled by amino acid amides as chiral bidentate directing groups. The use of an Ile-NH(2) auxiliary embedded in the substrate provided excellent levels of asymmetric induction (diastereomeric ratio of up to 72 : 1) in the Pd(ii)-catalyzed β-methylene C(sp(3))–H bond activation of cyclopropanes and cross-coupling with aryl iodides.
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spelling pubmed-56591702018-03-06 Asymmetric C–H functionalization of cyclopropanes using an isoleucine-NH(2) bidentate directing group Kim, Jinhee Sim, Mikyung Kim, Namhoon Hong, Sungwoo Chem Sci Chemistry The systematic investigation of substrate-bound α-amino acid auxiliaries has resulted in catalytic asymmetric C–H functionalization of cyclopropanes enabled by amino acid amides as chiral bidentate directing groups. The use of an Ile-NH(2) auxiliary embedded in the substrate provided excellent levels of asymmetric induction (diastereomeric ratio of up to 72 : 1) in the Pd(ii)-catalyzed β-methylene C(sp(3))–H bond activation of cyclopropanes and cross-coupling with aryl iodides. Royal Society of Chemistry 2015-06-01 2015-04-16 /pmc/articles/PMC5659170/ /pubmed/29511524 http://dx.doi.org/10.1039/c5sc01137j Text en This journal is © The Royal Society of Chemistry 2015 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Kim, Jinhee
Sim, Mikyung
Kim, Namhoon
Hong, Sungwoo
Asymmetric C–H functionalization of cyclopropanes using an isoleucine-NH(2) bidentate directing group
title Asymmetric C–H functionalization of cyclopropanes using an isoleucine-NH(2) bidentate directing group
title_full Asymmetric C–H functionalization of cyclopropanes using an isoleucine-NH(2) bidentate directing group
title_fullStr Asymmetric C–H functionalization of cyclopropanes using an isoleucine-NH(2) bidentate directing group
title_full_unstemmed Asymmetric C–H functionalization of cyclopropanes using an isoleucine-NH(2) bidentate directing group
title_short Asymmetric C–H functionalization of cyclopropanes using an isoleucine-NH(2) bidentate directing group
title_sort asymmetric c–h functionalization of cyclopropanes using an isoleucine-nh(2) bidentate directing group
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5659170/
https://www.ncbi.nlm.nih.gov/pubmed/29511524
http://dx.doi.org/10.1039/c5sc01137j
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AT kimnamhoon asymmetricchfunctionalizationofcyclopropanesusinganisoleucinenh2bidentatedirectinggroup
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