Mechanistic Basis for Rate Enhancements in the Methanolysis of Aliphatic Esters of Quinine

摘要

The famous alkaloid quinine (1) has a long history and has played an integral part in the development of organic chemistry and medicine. Cinchona extracts were introduced into medical use in Europe in the 17th century when the Countess of Chinchon in1638 was treated and cured of malaria. Pure quinine was isolated in 18202 setting the stage for over 150 years of biological, structural, and synthetic work. Remarkably, quinine has retained a prominent position among organic chemists where, most recently, the properties of this alkaloid as a chiral auxiliary and a ligand for asymmetric catalysis have been investigated.