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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| Format: | Article |
| Language: | English |
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MDPI AG
2018-08-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/23/8/2003 |
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| author | Takatsugu Murata Tatsuya Kawanishi Akihiro Sekiguchi Ryo Ishikawa Keisuke Ono Kenya Nakata Isamu Shiina |
| author_facet | Takatsugu Murata Tatsuya Kawanishi Akihiro Sekiguchi Ryo Ishikawa Keisuke Ono Kenya Nakata Isamu Shiina |
| author_sort | Takatsugu Murata |
| collection | DOAJ |
| 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. |
| first_indexed | 2024-12-21T01:29:09Z |
| format | Article |
| id | doaj.art-5bf908ddad6f4a7493f7776bac861ee4 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-21T01:29:09Z |
| publishDate | 2018-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-5bf908ddad6f4a7493f7776bac861ee42022-12-21T19:20:24ZengMDPI AGMolecules1420-30492018-08-01238200310.3390/molecules23082003molecules23082003Kinetic Resolution of Racemic 2-Hydroxyamides Using a Diphenylacetyl Component as an Acyl Source and a Chiral Acyl-Transfer CatalystTakatsugu Murata0Tatsuya Kawanishi1Akihiro Sekiguchi2Ryo Ishikawa3Keisuke Ono4Kenya Nakata5Isamu Shiina6Department of Appliaed Chemistry, Faculty of Science, Tokyo University of Science, Tokyo 162-8601, JapanDepartment of Appliaed Chemistry, Faculty of Science, Tokyo University of Science, Tokyo 162-8601, JapanDepartment of Appliaed Chemistry, Faculty of Science, Tokyo University of Science, Tokyo 162-8601, JapanDepartment of Appliaed Chemistry, Faculty of Science, Tokyo University of Science, Tokyo 162-8601, JapanDepartment of Appliaed Chemistry, Faculty of Science, Tokyo University of Science, Tokyo 162-8601, JapanGraduate School of Natural Science and Technology, Shimane University, Shimane 690-8504, JapanDepartment of Appliaed Chemistry, Faculty of Science, Tokyo University of Science, Tokyo 162-8601, JapanVarious 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.http://www.mdpi.com/1420-3049/23/8/2003kinetic resolution2-hydroxyamideorganocatalysisWeinreb amideesterificationcarboxylic anhydride |
| spellingShingle | Takatsugu Murata Tatsuya Kawanishi Akihiro Sekiguchi Ryo Ishikawa Keisuke Ono Kenya Nakata Isamu Shiina Kinetic Resolution of Racemic 2-Hydroxyamides Using a Diphenylacetyl Component as an Acyl Source and a Chiral Acyl-Transfer Catalyst Molecules kinetic resolution 2-hydroxyamide organocatalysis Weinreb amide esterification carboxylic anhydride |
| 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 | kinetic resolution 2-hydroxyamide organocatalysis Weinreb amide esterification carboxylic anhydride |
| url | http://www.mdpi.com/1420-3049/23/8/2003 |
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