Kinetic Resolution of Racemic 2-Hydroxyamides Using a Diphenylacetyl Component as an Acyl Source and a Chiral Acyl-Transfer Catalyst

Various optically active 2-hydroxyamide derivatives are produced based on the kinetic resolution of racemic 2-hydroxyamides with a diphenylacetyl component and (R)-benzotetramisole ((R)-BTM), a chiral acyl-transfer catalyst, via asymmetric esterification and acylation. It was revealed that a tertiar...

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Autores principales: Murata, Takatsugu, Kawanishi, Tatsuya, Sekiguchi, Akihiro, Ishikawa, Ryo, Ono, Keisuke, Nakata, Kenya, Shiina, Isamu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6222459/
https://www.ncbi.nlm.nih.gov/pubmed/30103468
http://dx.doi.org/10.3390/molecules23082003
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author Murata, Takatsugu
Kawanishi, Tatsuya
Sekiguchi, Akihiro
Ishikawa, Ryo
Ono, Keisuke
Nakata, Kenya
Shiina, Isamu
author_facet Murata, Takatsugu
Kawanishi, Tatsuya
Sekiguchi, Akihiro
Ishikawa, Ryo
Ono, Keisuke
Nakata, Kenya
Shiina, Isamu
author_sort Murata, Takatsugu
collection PubMed
description Various optically active 2-hydroxyamide derivatives are produced based on the kinetic resolution of racemic 2-hydroxyamides with a diphenylacetyl component and (R)-benzotetramisole ((R)-BTM), a chiral acyl-transfer catalyst, via asymmetric esterification and acylation. It was revealed that a tertiary amide can be used with this novel protocol to achieve high selectivity (22 examples; s-value reaching over 250). The resulting chiral compounds could be transformed into other useful structures while maintaining their chirality.
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spelling pubmed-62224592018-11-13 Kinetic Resolution of Racemic 2-Hydroxyamides Using a Diphenylacetyl Component as an Acyl Source and a Chiral Acyl-Transfer Catalyst Murata, Takatsugu Kawanishi, Tatsuya Sekiguchi, Akihiro Ishikawa, Ryo Ono, Keisuke Nakata, Kenya Shiina, Isamu Molecules Article Various optically active 2-hydroxyamide derivatives are produced based on the kinetic resolution of racemic 2-hydroxyamides with a diphenylacetyl component and (R)-benzotetramisole ((R)-BTM), a chiral acyl-transfer catalyst, via asymmetric esterification and acylation. It was revealed that a tertiary amide can be used with this novel protocol to achieve high selectivity (22 examples; s-value reaching over 250). The resulting chiral compounds could be transformed into other useful structures while maintaining their chirality. MDPI 2018-08-10 /pmc/articles/PMC6222459/ /pubmed/30103468 http://dx.doi.org/10.3390/molecules23082003 Text en © 2018 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 (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Murata, Takatsugu
Kawanishi, Tatsuya
Sekiguchi, Akihiro
Ishikawa, Ryo
Ono, Keisuke
Nakata, Kenya
Shiina, Isamu
Kinetic Resolution of Racemic 2-Hydroxyamides Using a Diphenylacetyl Component as an Acyl Source and a Chiral Acyl-Transfer Catalyst
title Kinetic Resolution of Racemic 2-Hydroxyamides Using a Diphenylacetyl Component as an Acyl Source and a Chiral Acyl-Transfer Catalyst
title_full Kinetic Resolution of Racemic 2-Hydroxyamides Using a Diphenylacetyl Component as an Acyl Source and a Chiral Acyl-Transfer Catalyst
title_fullStr Kinetic Resolution of Racemic 2-Hydroxyamides Using a Diphenylacetyl Component as an Acyl Source and a Chiral Acyl-Transfer Catalyst
title_full_unstemmed Kinetic Resolution of Racemic 2-Hydroxyamides Using a Diphenylacetyl Component as an Acyl Source and a Chiral Acyl-Transfer Catalyst
title_short Kinetic Resolution of Racemic 2-Hydroxyamides Using a Diphenylacetyl Component as an Acyl Source and a Chiral Acyl-Transfer Catalyst
title_sort kinetic resolution of racemic 2-hydroxyamides using a diphenylacetyl component as an acyl source and a chiral acyl-transfer catalyst
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6222459/
https://www.ncbi.nlm.nih.gov/pubmed/30103468
http://dx.doi.org/10.3390/molecules23082003
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