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

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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Bibliographic Details
Main Authors: Takatsugu Murata, Tatsuya Kawanishi, Akihiro Sekiguchi, Ryo Ishikawa, Keisuke Ono, Kenya Nakata, Isamu Shiina
Format: Article
Language:English
Published: MDPI AG 2018-08-01
Series:Molecules
Subjects:
kinetic resolution
2-hydroxyamide
organocatalysis
Weinreb amide
esterification
carboxylic anhydride
Online Access:http://www.mdpi.com/1420-3049/23/8/2003
Description
Summary: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.
ISSN:1420-3049

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