Biomimetic Catalysis of an SN2 Reaction Resulting from a Novel Form of Transition-State Stabilization.

摘要

Biomimetic catalysis of the Sn2 alkylation of quinoline-type nucleophiles is achieved when the nucleophile is bound in an electron-rich receptor site formed by a macrocyclic cyclophane. It is proposed that the high polarizability of the transition state enhances it binding to the receptor. This in turn leads to catalysis according to the Pauling model of transition-state binding.