2134/34126
Sylvain Blanc
Sylvain
Blanc
New reagents for asymmetric electrophilic nitrogen transfer
Loughborough University
2018
untagged
Chemical Sciences not elsewhere classified
2018-07-25 09:29:16
Thesis
https://repository.lboro.ac.uk/articles/thesis/New_reagents_for_asymmetric_electrophilic_nitrogen_transfer/9399530
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.]