Chiral ammonium betaine-catalyzed asymmetric Mannich-type reaction of oxindoles

A highly diastereo- and enantioselective Mannich-type reaction of 3-aryloxindoles with N-Boc aldimines was achieved under the catalysis of axially chiral ammonium betaines. This catalytic method provides a new tool for the construction of consecutive quaternary and tertiary stereogenic carbon center...

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Detalles Bibliográficos
Autores principales: Torii, Masahiro, Kato, Kohsuke, Uraguchi, Daisuke, Ooi, Takashi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2016
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5082719/
https://www.ncbi.nlm.nih.gov/pubmed/27829916
http://dx.doi.org/10.3762/bjoc.12.199
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author Torii, Masahiro
Kato, Kohsuke
Uraguchi, Daisuke
Ooi, Takashi
author_facet Torii, Masahiro
Kato, Kohsuke
Uraguchi, Daisuke
Ooi, Takashi
author_sort Torii, Masahiro
collection PubMed
description A highly diastereo- and enantioselective Mannich-type reaction of 3-aryloxindoles with N-Boc aldimines was achieved under the catalysis of axially chiral ammonium betaines. This catalytic method provides a new tool for the construction of consecutive quaternary and tertiary stereogenic carbon centers on biologically intriguing molecular frameworks with high fidelity.
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spelling pubmed-50827192016-11-09 Chiral ammonium betaine-catalyzed asymmetric Mannich-type reaction of oxindoles Torii, Masahiro Kato, Kohsuke Uraguchi, Daisuke Ooi, Takashi Beilstein J Org Chem Letter A highly diastereo- and enantioselective Mannich-type reaction of 3-aryloxindoles with N-Boc aldimines was achieved under the catalysis of axially chiral ammonium betaines. This catalytic method provides a new tool for the construction of consecutive quaternary and tertiary stereogenic carbon centers on biologically intriguing molecular frameworks with high fidelity. Beilstein-Institut 2016-09-28 /pmc/articles/PMC5082719/ /pubmed/27829916 http://dx.doi.org/10.3762/bjoc.12.199 Text en Copyright © 2016, Torii et al. https://creativecommons.org/licenses/by/4.0https://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/4.0), 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 Letter
Torii, Masahiro
Kato, Kohsuke
Uraguchi, Daisuke
Ooi, Takashi
Chiral ammonium betaine-catalyzed asymmetric Mannich-type reaction of oxindoles
title Chiral ammonium betaine-catalyzed asymmetric Mannich-type reaction of oxindoles
title_full Chiral ammonium betaine-catalyzed asymmetric Mannich-type reaction of oxindoles
title_fullStr Chiral ammonium betaine-catalyzed asymmetric Mannich-type reaction of oxindoles
title_full_unstemmed Chiral ammonium betaine-catalyzed asymmetric Mannich-type reaction of oxindoles
title_short Chiral ammonium betaine-catalyzed asymmetric Mannich-type reaction of oxindoles
title_sort chiral ammonium betaine-catalyzed asymmetric mannich-type reaction of oxindoles
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5082719/
https://www.ncbi.nlm.nih.gov/pubmed/27829916
http://dx.doi.org/10.3762/bjoc.12.199
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AT katokohsuke chiralammoniumbetainecatalyzedasymmetricmannichtypereactionofoxindoles
AT uraguchidaisuke chiralammoniumbetainecatalyzedasymmetricmannichtypereactionofoxindoles
AT ooitakashi chiralammoniumbetainecatalyzedasymmetricmannichtypereactionofoxindoles

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