A Useful Allene for the Stereoselective Synthesis of Protected Quaternary 2‑Amino-2-vinyl-1,3-diols

Treatment of readily available allene 1 with Cy₂BH followed by addition of an aldehyde led to quaternary protected 2-amino-2-vinyl-1,3-diols in high yield and excellent stereochemical purity. The choice of benzoyl as N-protecting group is critical since the observed N- to O-Bz transfer during the process prevents later undesired isomerizations in the adducts and keeps all heteroatoms protected.