Development of Guanidine-Bisurea Bifunctional Organocatalysts with a Chiral Pyrrolidine Moiety and Application to α-Hydroxylation of Tetralone-Derived β-Keto Esters

Novel guanidine-bisurea bifunctional organocatalysts 5 bearing a chiral pyrrolidine moiety on guanidine were designed with the guidance of DFT calculations. The resulting organocatalysts 5 were examined for α-hydroxylation of tetralone-derived β-keto esters, and good selectivity was obtained with 5j...

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Autores principales: Odagi, Minami, Takayama, Kan, Sato, Makoto, Yamanaka, Masahiro, Nagasawa, Kazuo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2015
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6331824/
https://www.ncbi.nlm.nih.gov/pubmed/26184142
http://dx.doi.org/10.3390/molecules200712590
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author Odagi, Minami
Takayama, Kan
Sato, Makoto
Yamanaka, Masahiro
Nagasawa, Kazuo
author_facet Odagi, Minami
Takayama, Kan
Sato, Makoto
Yamanaka, Masahiro
Nagasawa, Kazuo
author_sort Odagi, Minami
collection PubMed
description Novel guanidine-bisurea bifunctional organocatalysts 5 bearing a chiral pyrrolidine moiety on guanidine were designed with the guidance of DFT calculations. The resulting organocatalysts 5 were examined for α-hydroxylation of tetralone-derived β-keto esters, and good selectivity was obtained with 5j bearing a methoxymethyl ether-containing chiral pyrrolidine moiety.
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spelling pubmed-63318242019-01-24 Development of Guanidine-Bisurea Bifunctional Organocatalysts with a Chiral Pyrrolidine Moiety and Application to α-Hydroxylation of Tetralone-Derived β-Keto Esters Odagi, Minami Takayama, Kan Sato, Makoto Yamanaka, Masahiro Nagasawa, Kazuo Molecules Article Novel guanidine-bisurea bifunctional organocatalysts 5 bearing a chiral pyrrolidine moiety on guanidine were designed with the guidance of DFT calculations. The resulting organocatalysts 5 were examined for α-hydroxylation of tetralone-derived β-keto esters, and good selectivity was obtained with 5j bearing a methoxymethyl ether-containing chiral pyrrolidine moiety. MDPI 2015-07-10 /pmc/articles/PMC6331824/ /pubmed/26184142 http://dx.doi.org/10.3390/molecules200712590 Text en © 2015 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 license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Odagi, Minami
Takayama, Kan
Sato, Makoto
Yamanaka, Masahiro
Nagasawa, Kazuo
Development of Guanidine-Bisurea Bifunctional Organocatalysts with a Chiral Pyrrolidine Moiety and Application to α-Hydroxylation of Tetralone-Derived β-Keto Esters
title Development of Guanidine-Bisurea Bifunctional Organocatalysts with a Chiral Pyrrolidine Moiety and Application to α-Hydroxylation of Tetralone-Derived β-Keto Esters
title_full Development of Guanidine-Bisurea Bifunctional Organocatalysts with a Chiral Pyrrolidine Moiety and Application to α-Hydroxylation of Tetralone-Derived β-Keto Esters
title_fullStr Development of Guanidine-Bisurea Bifunctional Organocatalysts with a Chiral Pyrrolidine Moiety and Application to α-Hydroxylation of Tetralone-Derived β-Keto Esters
title_full_unstemmed Development of Guanidine-Bisurea Bifunctional Organocatalysts with a Chiral Pyrrolidine Moiety and Application to α-Hydroxylation of Tetralone-Derived β-Keto Esters
title_short Development of Guanidine-Bisurea Bifunctional Organocatalysts with a Chiral Pyrrolidine Moiety and Application to α-Hydroxylation of Tetralone-Derived β-Keto Esters
title_sort development of guanidine-bisurea bifunctional organocatalysts with a chiral pyrrolidine moiety and application to α-hydroxylation of tetralone-derived β-keto esters
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6331824/
https://www.ncbi.nlm.nih.gov/pubmed/26184142
http://dx.doi.org/10.3390/molecules200712590
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