Functional micellar catalysis. Part 7. Cleavage of activated enantiomeric substrates by chiral functional surfactant systems

Abstract

The cleavage of enantiomeric p-nitrophenyl derivatives of the N-methyl-N-1-[hydroxy(phenyl)methyl]-ethylcarbamate (3), the 1-methylheptyl carbonate (4) and the α-methoxyphenylacetate (5) in the presence of homomicelles of N-hexadecyl-N-methylephedrinium bromide (1) and co-micelles composed of N^α-myristoyl-L-histidine (2) and hexadecyltrimethylammonium bromide or (1) was investigated. Rate effects ranging from inhibition to large enhancements and enantioselectivities ranging from 1.0 to 3.3 were observed.