Catalytic asymmetric tandem Friedel–Crafts alkylation/Michael addition reaction for the synthesis of highly functionalized chromans

The enantioselective tandem Friedel–Crafts alkylation/Michael addition reaction of indoles with nitroolefin enoates catalyzed by a diphenylamine-linked bis(oxazoline)-Zn(OTf)(2) complex was investigated. This tandem reaction afforded functionalized chiral chromans in good yields with moderate to hig...

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Detalles Bibliográficos
Autores principales: Peng, Jiahuan, Du, Da-Ming
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2013
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3701415/
https://www.ncbi.nlm.nih.gov/pubmed/23843916
http://dx.doi.org/10.3762/bjoc.9.137
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author Peng, Jiahuan
Du, Da-Ming
author_facet Peng, Jiahuan
Du, Da-Ming
author_sort Peng, Jiahuan
collection PubMed
description The enantioselective tandem Friedel–Crafts alkylation/Michael addition reaction of indoles with nitroolefin enoates catalyzed by a diphenylamine-linked bis(oxazoline)-Zn(OTf)(2) complex was investigated. This tandem reaction afforded functionalized chiral chromans in good yields with moderate to high stereoselectivities (up to 95:5 dr, up to 99% ee).
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spelling pubmed-37014152013-07-10 Catalytic asymmetric tandem Friedel–Crafts alkylation/Michael addition reaction for the synthesis of highly functionalized chromans Peng, Jiahuan Du, Da-Ming Beilstein J Org Chem Full Research Paper The enantioselective tandem Friedel–Crafts alkylation/Michael addition reaction of indoles with nitroolefin enoates catalyzed by a diphenylamine-linked bis(oxazoline)-Zn(OTf)(2) complex was investigated. This tandem reaction afforded functionalized chiral chromans in good yields with moderate to high stereoselectivities (up to 95:5 dr, up to 99% ee). Beilstein-Institut 2013-06-24 /pmc/articles/PMC3701415/ /pubmed/23843916 http://dx.doi.org/10.3762/bjoc.9.137 Text en Copyright © 2013, Peng and Du https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Peng, Jiahuan
Du, Da-Ming
Catalytic asymmetric tandem Friedel–Crafts alkylation/Michael addition reaction for the synthesis of highly functionalized chromans
title Catalytic asymmetric tandem Friedel–Crafts alkylation/Michael addition reaction for the synthesis of highly functionalized chromans
title_full Catalytic asymmetric tandem Friedel–Crafts alkylation/Michael addition reaction for the synthesis of highly functionalized chromans
title_fullStr Catalytic asymmetric tandem Friedel–Crafts alkylation/Michael addition reaction for the synthesis of highly functionalized chromans
title_full_unstemmed Catalytic asymmetric tandem Friedel–Crafts alkylation/Michael addition reaction for the synthesis of highly functionalized chromans
title_short Catalytic asymmetric tandem Friedel–Crafts alkylation/Michael addition reaction for the synthesis of highly functionalized chromans
title_sort catalytic asymmetric tandem friedel–crafts alkylation/michael addition reaction for the synthesis of highly functionalized chromans
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3701415/
https://www.ncbi.nlm.nih.gov/pubmed/23843916
http://dx.doi.org/10.3762/bjoc.9.137
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