70959-98-7Relevant articles and documents
Synergistic Peptide and Gold Catalysis: Enantioselective Addition of Branched Aldehydes to Allenamides
Nicholls, Leo D. M.,Wennemers, Helma
supporting information, p. 17559 - 17564 (2021/10/19)
The combination of a peptide catalyst and a gold catalyst is presented for enantioselective addition reactions between branched aldehydes and allenamides. The two catalysts act in concert to provide γ,δ-enamide aldehydes bearing a fully substituted, benzylic stereogenic center – a structural motif common in many natural products and therapeutically active compounds – with good yields and enantioselectivities. The reaction tolerates a variety of alkyl and alkoxy substituted aldehydes and the products can be elaborated into several chiral building blocks bearing either 1,4- or 1,5- functional group relationships. Mechanistic studies showed that the conformational features of the peptide are important for both the catalytic efficiency and stereochemistry, while a balance of acid/base additives is key for ensuring formation of the desired product over undesired side reactions.
Zirconium triflate grafted on SBA-15 as a highly efficient solid acid catalyst for ring opening of epoxides by amines and alcohols
Tayade, Kamlesh N.,Wang, Lianyue,Shang, Sensen,Dai, Wen,Mishra, Manish,Gao, Shuang
, p. 758 - 766 (2017/04/24)
Metal (Al, Ti, Zr) triflate grafted mesoporous SBA-15 (AlTf/S, TiTf/S, ZrTf/S) samples were synthesized as inexpensive solid acid materials by a simple one-pot-two-step synthesis methodology. These materials were characterized by X-ray diffraction, N2-sorption, thermogravimetric analysis, Fourier transform infrared spectroscopy (FT-IR), in-situ pyridine FT-IR spectroscopy, and elemental analysis. ZrTf/S was found to be a highly efficient and reusable solid acid catalyst for ring opening of epoxides with amines and alcohols and produced β-amino alcohols and β-alkoxy alcohols respectively under ambient reaction conditions. The ZrTf/S catalyst showed the highest activity, which was attributed to its high acidity compared with that of the Ti and Al containing samples.
Lanthanide-based coordination polymers as promising heterogeneous catalysts for ring-opening reactions
Kumar, Gulshan,Kumar, Girijesh,Gupta, Rajeev
, p. 21352 - 21361 (2016/03/08)
This work presents the synthesis and structural characterization of Eu3+- and Tb3+-based coordination polymers starting from a Co3+-based metalloligand offering appended arylcarboxylic acid groups. Both coordination polymers function as reusable heterogeneous catalysts for ring-opening reactions utilizing amines, alcohols, thiols, and azides as the nucleophiles. The catalytic results illustrate an excellent control over the regioselectivity whereas a filtration test and mechanistic studies substantiate Lewis-acid catalyzed activation of the epoxide during the reaction.