Amino alcohols are important constituents of biologically active molecules (Figure ) and have inspired the invention of many elegant techniques for their construction (Scheme 1). Pioneering efforts on syntheses of vicinal amino alcohols have focused on transition metal catalyzed processes to install both N-and Omoieties in a single transformation. A complementary approach is the ring-opening of epoxides with Nnucleophiles and of aziridines with O-nucleophiles. This untethered approach is convenient from the perspective of step counts, but challenges with regiocontrol often result in intractable product mixtures. Temporary tethering using Lewis acid templates affords excellent regiocontrol with epoxides, but only one such report exists with aziridines. Our laboratory has a programmatic focus on the development of the di-tert-butyl-silanol auxiliary into a uniquely reactive functional handle. We envisioned a ring-opening of aziridines by pendant di-tert-butyl silanol auxiliaries, which would afford protected amino alcohols in a single transformation. Here, we show our development of this reaction, and its application in the rapid assembly of select natural products and analogues.