Synthesis of chiral cage annulated macrocycles.

Abstract

Chiral crown ethers have recently been shown to be useful asymmetric catalysts in many carbon-carbon bond forming reactions. The design and synthesis of new chiral macrocycles and ligands for use in asymmetric catalysis is of great interest in the field of synthetic chemistry. Catalytic asymmetric Michael additions have been studied using chiral crown ethers as phase transfer catalysts. Many chiral crown ethers have been synthesised and tested in asymmetric catalysis but the design of these systems is still an area of much interest. The attempted synthesis of a new class of novel macrocycles such as 1 is described (chapter 2). The synthesis of a new class of chiral cage annulated macrocycles such as 2 is reported (chapter 3). The testing of these macrocycles as catalysts in the Michael addition of 2-nitropropane to chalcone was carried out with poor enantioselectivity being observed Recognition events in chemistry occur on a molecular scale that is difficult to monitor without the use of molecular devices. Photoinduced Electron Transfer (PET) systems have been the subject of much research over the past three decades. The attempted synthesis of the first chiral PET sensor 3 is described (chapter 4).