“…In continuation of our previous studies on the introduction of new catalysts for the promotion of multi‐component reactions [44–48] and specially bio‐organic ones, [49–51] in this investigation concurrent generation of carboxylic acids from the aerobic oxidation of aldehydes leading to α ‐acyloxycarboxamides with an stereogenic center and considerable ee by the supporting role of Pregabalin as an efficient reagent under the auxiliary of water is reported. It should be noted that although the role of amino acids in reaction with isocyanide and aldehydes was studied in the Ugi's reaction, [52–53] in this work we showed that by changing of the solvent and temperature the same reaction can lead to the production of the asymmetric Passerini's products (Scheme 3).…”
This article describes the use of Pregabalin as a commercially available chiral amino acid in the efficient synthesis of the Passerini‐type condensation products via two‐component condensation of aromatic aldehydes with cyclohexyl isocyanide. All reactions are accompanied with aerobic oxidation of aldehydes in water leading to chiral α‐acyloxycarboxamides with moderate to good enantioselectivities (up to 88 % ee) under green conditions such as nonmetal source. This is the first report of asymmetric synthesis of Passerini products in water.
“…In continuation of our previous studies on the introduction of new catalysts for the promotion of multi‐component reactions [44–48] and specially bio‐organic ones, [49–51] in this investigation concurrent generation of carboxylic acids from the aerobic oxidation of aldehydes leading to α ‐acyloxycarboxamides with an stereogenic center and considerable ee by the supporting role of Pregabalin as an efficient reagent under the auxiliary of water is reported. It should be noted that although the role of amino acids in reaction with isocyanide and aldehydes was studied in the Ugi's reaction, [52–53] in this work we showed that by changing of the solvent and temperature the same reaction can lead to the production of the asymmetric Passerini's products (Scheme 3).…”
This article describes the use of Pregabalin as a commercially available chiral amino acid in the efficient synthesis of the Passerini‐type condensation products via two‐component condensation of aromatic aldehydes with cyclohexyl isocyanide. All reactions are accompanied with aerobic oxidation of aldehydes in water leading to chiral α‐acyloxycarboxamides with moderate to good enantioselectivities (up to 88 % ee) under green conditions such as nonmetal source. This is the first report of asymmetric synthesis of Passerini products in water.
“…Aer extensive studies on the introduction and application of various catalysts in our research group, [45][46][47][48][49][50][51] and especially the use of nano-catalysts such as piperazine immobilized on nano-ZnO-sulfuric acid (PINZS) and piperazinium nano silica sulfonate (PNSS) in the synthesis of some organic compounds, 52,53 in this research we decided to compare the catalytic properties of PINZS and PNSS in the synthesis of benzimidazole and benzoxazole derivatives. This research shows the importance of choosing of the appropriate support in the immobilization of ionic liquids.…”
In this work, a comparison between the catalytic activity of two piperazine based ionic liquids immobilized on ZnO NPs and SiO2 NPs is presented in the synthesis of benzoxazoles and benzimidazoles.
“…The above mentioned catalysts have high yields, [6][7][8]11 short reaction times, 7,10,11 easy work-up procedure, 7,10,11 solvent-free condition 6,11 and reusability of catalyst. 12 Some procedures have disadvantages such as strong acid condition 10 and no reusability catalyst. [8][9][10] Sb(III) is a good Lewis acid for activation of carbonyl compound.…”
Section: Introductionmentioning
confidence: 99%
“…The above mentioned catalysts have high yields, 6–8,11 short reaction times, 7,10,11 easy work-up procedure, 7,10,11 solvent-free condition 6,11 and reusability of catalyst. 12…”
Sb(iii)–Gum Arabic composite as a unique natural-based and nontoxic catalyst was synthesized and characterized by FT-IR, XRD, TGA, ICP, BET, EDX and mapping.
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