AbstractN-Acyl imidazolidinones are key intermediates in the stereoselective synthesis of amino acids as shown by ‘self-regeneration of stereochemistry’ methods. This thesis reports a diastereoselective synthesis of trans Nchloroformylimidazolidinones,
species which represent a powerful new template for the generation of a
wide range of unnatural amino acid derivatives. In addition to classical alkylations, it also describes a number of other reactions in which the N-chloroformylimidazolidinone plays a pivotal role. The thesis gives an
overview of the development, scope and mechanistic studies of the N-chloroformylimidazolidinone not only in asymmetric alkylation, but also in mild Friedel-Crafts acylative cyclisations. It shows how these new versions of aromatic and aliphatic Bischler–Napieralski reactions can be used to generate highly functionalised 3,4-dihydroisoquinolones and pipecolic acid derivatives in enantioenriched form.
|Date of Award||29 Sep 2020|
|Supervisor||Jonathan Clayden (Supervisor)|