Our success with the range of substrates shown in Schemes 4 and 5 prompted us to apply this reaction as a key step in the assembly of a variety of sphingosine-type natural products, a storied class whose members have demonstrated biological activity. Commercially available (E)-dodec-2-en-1-ol was converted into silanol 51 using our laboratory's standard silylation protocol (Scheme 6A). A Kürti aziridination followed by acetylation gave cyclization precursor 53. Cyclization with Ph3C + BF4 -/NaHCO3 formed 54 in a 75% yield. TBAF removal of the silyl group yielded (±)-Clavaminol H which could be converted into (±)-des-acetyl-Clavaminol H upon heating with 6M aqueous HCl solution. A similar strategy was applied for the synthesis of (±)-N-hexanoyldihydrosphingosine (Scheme 6B). (±)-N-hexanoyldihydrosphingosine is commercially available, but, to our knowledge, ours is the first synthesis of this target. Protecting 56 with CbzCl followed by our BINOLphosphoric acid promoted cyclization furnished key intermediate 60, which was then globally deprotected into (±)-Dihydrosphingosine (Scheme 6C). In summary, we present a unique strategy for the synthesis of vicinal amino alcohols. Ring opening of aziridines with pendant silanols is compatible with a variety of N-substituents and alkyl chains. The utility of this methodology is demonstrated via facile preparations of (±)-Clavaminol H, (±)-Dihydrosphingosine, (±)-N-Hexanoyldihydrosphingosine, and (±)-des-acetyl-Clavaminol H. Given the ubiquity of the vicinal amino alcohol motif in targets of value, this technology is a welcome addition to the synthetic armory.