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Molecules 2018, 23(8), 2003; https://doi.org/10.3390/molecules23082003

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

1
Department of Appliaed Chemistry, Faculty of Science, Tokyo University of Science, Tokyo 162-8601, Japan
2
Graduate School of Natural Science and Technology, Shimane University, Shimane 690-8504, Japan
*
Authors to whom correspondence should be addressed.
Received: 23 July 2018 / Revised: 6 August 2018 / Accepted: 7 August 2018 / Published: 10 August 2018
(This article belongs to the Special Issue Stereogenic Centers)
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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. View Full-Text
Keywords: kinetic resolution; 2-hydroxyamide; organocatalysis; Weinreb amide; esterification; carboxylic anhydride kinetic resolution; 2-hydroxyamide; organocatalysis; Weinreb amide; esterification; carboxylic anhydride
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Murata, T.; Kawanishi, T.; Sekiguchi, A.; Ishikawa, R.; Ono, K.; Nakata, K.; Shiina, I. Kinetic Resolution of Racemic 2-Hydroxyamides Using a Diphenylacetyl Component as an Acyl Source and a Chiral Acyl-Transfer Catalyst. Molecules 2018, 23, 2003.

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