Atkinson’s aziridination

A full report has now been published on the asymmetric version of Atkinson s aziridination of activated alkenes.56... 

In 1999, Bob Atkinson wrote [1] that aziridination reactions were epoxida-tion s poor relation , and this was undoubtedly true at that time the scope of the synthetic methods available for preparation of aziridines was rather narrow when compared to the diversity of the procedures used for the preparation of the analogous oxygenated heterocycles. The preparation of aziridines has formed the basis of several reviews [2] and the reader is directed towards those works for a comprehensive analysis of the area this chapter presents a concise overview of classical methods and focuses on modern advances in the area of aziridine synthesis, with particular attention to stereoselective reactions between nitrenes and al-kenes on the one hand, and carbenes and imines on the other. 

I particularly acknowledge the support of my colleague, Dr Robert S. Atkinson, who read most of the manuscript, and whose help was instrumental in preparing the chapter on aziridination. 

Although the first aziridine was synthesized by Gabriel in 1888, aziridination reactions were still being described by Atkinson as epoxidation s poor relation in 1999 [36], This statement dramatically reflects some of the inherent difficulties associated with the development of effective methods to synthesize aziridines. Traditionally, chiral aziridines have typically been formed by multistep procedures from chiral alcohol precursors, such as the corresponding /3-amino alcohols [34, 35]. More specialized methods have also been developed, as illustrated by Heathcock s two-step sequence proceeding through /3-iodo carbamate 170 (Scheme 9.21) [138]. 

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