Ring Opening of Nonactivated 2-(1-Aminoalkyl) Aziridines:  Unusual Regio- and Stereoselective C-2 and C-3 Cleavage

We have studied the ring opening of nonactivated amino aziridines 1 by water under acidic conditions. Depending on the acid used, amino aziridines are cleaved at C-3 or C-2 with high regioselectivity, and total stereoselectivity, affording chiral 2,3-diaminoalkan-1-ols 3 or 1,3-diaminoalkan-2-ols 4 in high yield.