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 (<italic>R</italic>)-benzotetramisole ((<italic>R</italic>)-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; <italic>s</italic>-value reaching over 250). The resulting chiral compounds could be transformed into other useful structures while maintaining their chirality. [ABSTRACT FROM AUTHOR]