Synthesis and stereoselective lithiation of enantiopure 2‐(1‐aminoalkyl)aziridine–borane complexes

Abstract

This work shows that the enantiopure 2-(1-aminoalkyl)aziridine–borane complexes can easily be obtained by two alternative methodologies: either reaction with BF3·Et2O followed by reduction with LiAlH4 or by direct reaction with a solution of BH3 in THF. In addition, regio- and stereoselective C3 deuteration or silylation of 2-(1- aminoalkyl)aziridine 1 can be effected by eprotonation/ deuteration or silylation/decomplexation of the corresponding borane complex 2. Application of this methodology to functionalize 2-(1-aminoalkyl)aziridines with other different electrophiles is currently under investigation.