Stereoselective Synthesis using N-Chloroformylimidazolidinones

  • Mostafa Mahmoud Amer

Student thesis: Doctoral ThesisDoctor of Philosophy (PhD)

Abstract

N-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 Award29 Sep 2020
Original languageEnglish
Awarding Institution
  • The University of Bristol
SupervisorJonathan P Clayden (Supervisor)

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