Studies On The Intramolecular Aldol Reaction Via Enantioselective Desymmetrization

Asymmetric organic synthesis is one of the most attractive research areas in organic synthesis. As a new method for asymmetric synthesis, enantioselective organocatalysis is more and more popular. The asymmetric aldol reaction is considered to be one of the important reaction of the carbon-carbon bond forming. It provides an atom-economic approach toβ-hydroxy-carbonyls which make up a large family of chiral intermediates for synthesis of many drugs. As the development of asymmetric chemistry, asymmetric Aldol reaction catalyzed by the small organic molecule has become a hot research topic in organic chemistry in recent years.The desymmetrization of meso compounds has become one of the most powerful strategies in organic synthesis. It allows the formation of multiple chiral centers in a single step and offers an entry to a wide range of stereochemically complex molecules including natural products. The main advantage of the desymmetrization reactions is that symmetric precursors are readily accessible and easily synthesized.Construction of chiral quaternary carbon has been a key and difficult point of organic synthesis research, it has important meaning for the development and application of organic synthesis. This thesis is focused on the intramolecular desymmetric Aldol reaction. On the catalysis of the Br(?)nsted Acid and quinine amine, prochiral compounds containing quaternary carbon center, a step transformation delivered the [3.3.1] bridge ring compound containing three chiral centers by the intramolecular desymmetric Aldol reaction, at the same time, the chiral quaternary carbon was effectively constructed.