Oxaziridines

Introduction

Oxaziridines were first discovered in 1956 [1] and have been widely investigated, principally for two reasons. The ­presence of an inherently weak N-O bond in a strained ring promised a group of compounds of unusually high ­reactivity. In addition, this system possesses the structural elements that seem to be required in order to observe ­stereochemical isomerism at nitrogen: ring strain and an atom with unshared electron pairs attached to the ­nitrogen.

Oxaziridines can be used as both oxygenating and aminating agents in their reactions with a wide variety of nucleophiles. Oxaziridines with small groups on N, for example hydrogen or methyl, act as aminating agents, whereas those with bulky or electron withdrawing groups on N preferentially transfer the oxygen atom. Oxaziridine-­mediated processes are of interest due to the easy accessibility of the reagents and their potential for asymmetric ­induction.

References

• 1 Emmons WD. J. Am. Chem. Soc.  1956,  78:  6208 
• 2 Evans DA. Morrissey MM. Dorow RL. J. Am. Chem. Soc.  1985,  107:  4346 
• 3 Davis FA. Sheppard AC. Chen B.-C. Serajul Haque M. J. Am. Chem. Soc.  1990,  112:  6679 
• 4 Davis FA. Abdul-Malik NF. Awad SB. Harakal ME. Tetrahedron Lett.  1981,  22:  917 
• 5 Arnone A. Desmarteau DD. Novo V. Petrov VA. Pregnolato M. Resnati G. J. Org. Chem.  1996,  61:  8805 
• 6 Andreae S. Schmitz E. Synthesis  1991,  327 
• 7 Schmitz E. Fechner-Simon H. Schramm S. Liebigs Ann. Chem.  1969,  725:  1