Science of Synthesis

Aggarwal, V. K.; McGarrigle, E. M.; Shaw, M. A., Science of Synthesis: Stereoselective Synthesis, (2011) 2, 332.

Imines can be converted into aziridines through reaction with sulfur ylides. This reaction is often termed the aza-Corey–Chaykovsky reaction, by analogy to the Corey–Chaykovsky epoxidation of aldehydes described in Section ‌2.6.1.1‌, and was reported by the same investigators. As was the case with the previously described epoxidations, this reaction has been rendered asymmetric through the use of chiral sulfides, and this area has been reviewed.[‌25‌] In the case of imine aziridination, however, an alternative option exists for asymmetric synthesis, in that a chiral nitrogen protecting group can be employed to create a chiral environment. Both of these strategies have been used to good effect, and are discussed in turn in Sections ‌2.6.3.1.2‌ and ‌2.6.3.1.3‌, following a discussion of racemic systems. This chemistry has been described in Science of Synthesis, Vol. 40a [Amines and Ammonium Salts (Section 40.1.5.1.2.3)].

References