Aziridine, dynamic kinetic asymmetric

A dynamic kinetic asymmetric transformation (DYKAT) of racemic vinyl aziridine 347 yielded the enantiopure imidazolidinone 348 (Scheme 90) <20050L823>. This transformation was the initial step in a total synthesis of (+)-pseudodistomin D. 

Related reactions of vinylaziridines [79] or activated vinylcyclopropanes [80] with isocyanates and other heterocumulenes have been developed for the construction of cyclic ureas and similar heterocydes. For example, Trost has recently described a dynamic kinetic asymmetric reaction of aziridine 105 with phenylisocyanate that... 

By analogy to the DYKAT reactions with vinyl epoxides, Trost et al. have developed the Pd-eatalysed asymmetric dynamic kinetic allylic amination and acyl migration of vinyl aziridines with benzoyl imido carboxylates. As shown in Scheme 2.51, the process afforded the corresponding protected vicinal diamines in high yields and enantioselectivities of up to 93% ee. This methodology was demonstrated to be a platform for the formal synthesis of (-I- )-balanol and analogues. 

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