Chemoselective synthesis of β-amino acid derivatives by hydroamination of activated olefins using AlSBA-15 catalyst prepared by post-synthetic treatment

Abstract β-Amino acid derivatives have a wide variety of applications viz . in the synthesis of peptide analogues, precursor for amino alcohols, optically active amino acids, lactums and diamines. Chemoselective anti-Markovnikov hydroamination reaction of activated olefins was effectively used to synthesize β-amino acid derivatives using AlSBA-15 and AlMCM-41 catalysts. These catalysts with different Si/Al ratios were synthesized by isomorphous substitution of aluminium into the framework of SBA-15, which induces the Bronsted and Lewis acid sites. The structural integrity of the catalysts was established by characterizing with XRD, N 2 -sorption, TEM, NH 3 -TPD, 27 Al MAS NMR and 29 Si MAS NMR techniques. Hydroamination of ethyl acrylate with aniline was used as a test reaction, which gave N -[2-(ethoxycarbonyl)ethyl]aniline with high selectivity. The performance of AlSBA-15 catalyst was also determined with different acrylates and amines to know the general applicability of the catalyst in hydroamination reactions.