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

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 Brönsted and Lewis acid sites. The structural integrity of the catalysts was established by characterizing with XRD, N2-sorption, TEM, NH3-TPD, 27Al MAS NMR and 29Si 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.

Graphical abstractChemoselective anti-Markovnikov hydroamination reaction of activated olefins was effectively used to synthesize β-amino acid derivatives using AlSBA-15 catalyst. The reaction depends on the total acidity in the catalyst and both Brönsted and Lewis acid sites are active centers for this reaction.Figure optionsDownload full-size imageDownload as PowerPoint slide