Stereoselective Functionalization of 2-(1-Aminoalkyl)aziridines via Lithiation of Aziridine-Borane Complexes

Highly selective functionalization of the aziridine ring of (2S,1′S)‐2‐(1′‐aminoalkyl)aziridines 1, through successive formation of aziridine–borane complexes, lithiation, treatment with a variety of electrophiles and final decomplexation is described. The influence of the structure of the starting complexes 2 and of the electrophiles in the stereoselectivity of this process has been studied. Finally, successive double lithiation–electrophile reactions were carried out affording enantiopure 1,2,3,3‐tetrasubstituted aziridine–borane complexes with high selectivity. Se describe la funcionalización altamente selectiva de (2S,1′S)‐2‐(1′‐aminoalquil)aziridinas 1 a través de un proceso de formación de complejos borano–aziridina, litiación, tratamiento con electrófilos y descomplejación. También ha sido objeto de estudio la influencia de la estructura de los complejos 2 y de los electrófilos en el proceso. Finalmente, se ha llevado a cabo una doble reacción litiación y reacción con electrófilos dando lugar a complejos borano–aziridina 1,2,3,3‐tetrasustituidas de forma enantiopura y con alta selectividad. Highly selective functionalization of aziridine–borane complexes 1, through successive lithiation, treatment with different electrophiles and final decomplexation is described. Successive double lithiation–electrophile reactions were carried out affording enantiopure 1,2,3,3‐tetrasubstituted aziridine–borane complexes 2 with high selectivity.