New reagents for asymmetric electrophilic nitrogen transfer
thesisposted on 25.07.2018 by Sylvain Blanc
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This thesis describes the synthesis of new chiral NH oxaziridines and their uses for electrophilic amination reactions. The introduction highlights some of the most successful electrophilic amination reagents and development of systems for the formation of carbon-nitrogen bonds. Examples of the use of camphor and fenchone NH-oxaziridines synthesized by our group are provided towards the end of the first chapter. The second chapter is dedicated to our efforts to synthesize new chiral NH-oxaziridines derived from camphor. The first part of this chapter describes the formation of 3-mono- and 3,3-disubstituted camphor nitrimine precursors. The synthesis of 3-alkyl-camphor nitrimines and their attempted conversion to oxaziridines are reported in section 2.2. Section 2.3 concerns the synthesis of 3-halo-camphor oxaziridines, and the section 2.4 attempts to synthesize 3,3-dihalo-camphor oxaziridines. Investigation of the process of ammonolysis of camphor nitrimine using ammonia is discussed in section 2.5. Section 2.6 is dedicated to the attempted formation of 3,3-diacetal camphor nitrimines. [Continues.]