Selective Micellar Catalysis with Histidinyl Surfactants of Defined Absolute Configuration

Abstract

The stereoselectivity of the micellar-catalyzed hydrolysis of amino acid esters (2) by the histidinyl surfactants (1) strongly depends on their absolute configuration: In presence of the R,S-configurated surfactant (1), which like the S,S-diastereomer was also prepared in a few steps from γ-butyrolactone, S-(2) hydrolyzes 2.5 times as fast as R-(2).