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Published on: April 10, 2020
Kinetic Resolution of Racemic 2-Hydroxyamides Using a Diphenylacetyl Component as an Acyl Source and a Chiral
Takatsugu Murata1, Tatsuya Kawanishi2, Akihiro Sekiguchi3
1Department of Appliaed Chemistry, Faculty of Science, Tokyo University of Science, Tokyo 162-8601, Japan. b116707@ed.tus.ac.jp.
Abstract:
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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