MULTICOMPONENT, BROMONIUM ION INDUCED OLEFIN FUNCTIONALIZATION AND THE SYNTHETIC APPLICATIONS THEREOF

Abstract

Electrophilic activation of olefin by halogen source followed by nucleophilic attack constitutes one of the largest classes of reaction used to form chemo-, regio- and stereoselective carbon-heteroatom bond. In this thesis, a novel multicomponent bromonium ion induced epoxide ring opening reaction was described. Epichlorohydrin was used as one of the key components to achieve high regioselectivity. To further explore the potential of this methodology, the total synthesis of a Carnitine Acetyltransferase inhibitor and the preparation of an antidepressant drug (Reboxetine) were studied. The method provided a multicomponent strategy for the construction of highly functionalized morpholine compounds. In addition, bromonium ion induced aziridine ring expansion cascade reaction was conducted. The azepane products could be transformed into a number of functional molecules including piperidines, a bicyclic amine, and a bridgehead amide. In conclusion, bromonium ion induced epoxide ring opening reaction and brominium ion induced aziridine ring expansion cascade reaction were discovered. These reactions were applied in the preparation of functionalized aza-cyclic compounds, such as morpholines, azepanes, and piperidines etc.