Synthesis of chiral N-protected α-amino aldehydes by reduction of N-protected N-carboxyanhydrides (UNCAs)

Abstract

A facile one step synthesis of a wide variety of N-protected (Boc, Z, Fmoc) α-amino aldehydes under mild conditions is described. Pure N-protected (Boc, Z, Fmoc) α-amino aldehydes were obtained in high yields by reduction of N-protected (Z, Boc, Fmoc)-N-carboxyanhydrides (UNCAs) with equivalent amounts of lithium tris(tertbutoxy)aluminium hydride [LiAlH(O-t-Bu) 3] or lithium tris[(3-ethyl-3-pentyl)oxy]aluminium hydride (LTEPA) in THF as solvent. The reaction is simple, rapid and proceeds without detectable racemization.