Chemoselective synthesis of beta-amino acid derivatives by hydroamination of activated olefins using AISBA-15 catalyst prepared by post-synthetic treatment
Title | Chemoselective synthesis of beta-amino acid derivatives by hydroamination of activated olefins using AISBA-15 catalyst prepared by post-synthetic treatment |
Publication Type | Journal Article |
Year of Publication | 2008 |
Authors | Shanbhag, GV, Kumbar, SM, Halligudi, SB |
Journal | Journal of Molecular Catalysis A-Chemical |
Volume | 284 |
Issue | 1-2 |
Pagination | 16-23 |
Date Published | APR |
Type of Article | Article |
ISSN | 1381-1169 |
Keywords | acrylate, activated olefin, addition, AlMCM-41, AlSBA-15, Amine, beta-amino acid, Catalyst, hydroamination, Mesoporous |
Abstract | beta-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 beta-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, NH3-TPD Al-27 MAS NMR and Si-29 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. (C) 2008 Elsevier B.V. All rights reserved. |
DOI | 10.1016/j.molcata.2007.12.025 |
Type of Journal (Indian or Foreign) | Foreign |
Impact Factor (IF) | 3.958 |