N-hydroxymethyl group for configurationally stable N-alkoxycarbonyl α- amino aldehydes [1]

Article abstract of DOI:10.1016/S0040-4039(98)00715-1

Attachment of an N-hydroxymethyl group to N-Boc-α-amino aldehyde enhanced greatly the configurational stability of the stereogenic carbon α to the aldehyde group by shifting the equilibrium from an open form of ω- hydroxyaldehyde to a closed form of hemiacetal. The N-hydroxymethyl group was introduced by treating N-Boc-α-amino acids with formaldehyde in the presence of an acid catalyst followed by reduction with DIBALH.