SYNTHESIS OF CHIRAL N-PROTECTED ALPHA-AMINO ALDEHYDES BY REDUCTION OFN-PROTECTED N-CARBOXYANHYDRIDES (UNCAS)

A facile one step synthesis of a wide variety of N-protected (Boc, Z, Fmoc) alpha-amino aldehydes under mild conditions is described. Pure N -protected (Dec, Z, Fmoc) alpha-amino aldehydes were obtained in high yields by reduction of N-protected (Z, Dec, Fmoc)-N-carboxyanhydrides (UMCAs) with equivalent amounts of lithium tris(tert-butoxy)aluminium hydride [LiAlH(O-t-I3u)(3)] or lithium tris[(3-ethyl-3-pentyl)oxy]alum inium hydride (LTEPA) in THF as solvent. The reaction is simple, rapid and proceeds without detectable racemization.