Nonlinear effects at the soft interface of an emulsion in the List–Lerner–Barbas aldol reaction

Abstract

Nonlinear effects have been observed for the List–Lerner–Barbas aldol reaction catalyzed by a proline-based surfactant catalyst at the aqueous–organic interface under emulsifying conditions. The differential partitioning of the amphiphilic catalyst enantiomers at the interfacial assembly leads to deracemization at the soft interface of an emulsion. The effect cascades to the interfacial chemical processes, which reflect the asymmetry of the interacting chiral assembly. The observations establish that soft interfaces such as those present in an emulsion can present a platform for inducing asymmetric partitioning of catalysts and hence, lead to an apparently nonlinear trend in the induced chirality for interfacial processes.