New transformations of azacycles

Thesis

The work presented in this thesis involves new transformations of azacycles, focusing on the introduction of functionality α-to N. α-C-H functionalisation on an azetidine has been a long-standing challenge, with N-protecting/activating groups that work well in the higher and lower azacyclic systems not viable. A recent breakthrough in the Hodgson group showed the rarely used N-thiopivaloyl group was effective for α-deprotonation– electrophile trapping on azetidines, but was not without limitations concerning harsh removal conditions and scope for further substitutions. This thesis describes efforts to overcome these issues by development of a new protecting/activating group for N, t-butoxythiocarbonyl (Botc).

Authors: Mortimer, C

• DOI: 10.5287/ora-ozjoqe2q4
• Type of award: DPhil
• Level of award: Doctoral
• Awarding institution: University of Oxford
• Language: English
• Keywords: organic chemistry; azetidine; azacycles; asymmetric synthesis; heterocycles; organolithium
• Subjects: Heterocyclic chemistry; Azacycles; Asymmetric synthesis; Azetidine; Chemistry, Organic; Organolithium compounds; Lithiation