Post-synthetic modifications of Phenylalanine containing peptides by C-H olefination

Identifier:  TFG:1205

Handle: https://hdl.handle.net/20.500.11797/TFG1205

Authors:  Rodríguez Rubio, Arnau

Abstract:
The use of transition metals in catalysis has been studied during the last decades. However, it has been in the last few years when the most prevalent bond in organic chemistry, carbon-hydrogen, has become an object of study to researchers. This new method results in the formation of a highly desirable carbon-carbon or carbon-heteroatom bond. The present dissertation has been about the synthesis of dipeptides and its olefination reactions through C-H activation methods. The previous work done for methyl acetylglycyl-L-phenylalaninate (Ac-Gly-Phe-OMe) served as a method for the trials with the newly proposed methyl acetyl-L-phenylalanylglycinate (Ac-Phe-Gly-OMe). Different issues were found throughout all both synthetic and further olefination processes which are detailed and discussed later on as well as a proposal for the reaction mechanism and the transition states that are involved. Future work has been appointed in order to confirm such theory.