Synthesis of Quaternary-Carbon-Containing β2,2-Amino Acids by the RhI-Catalyzed Enantioselective Arylation of α-Substituted β-Nitroacrylates
| Autor: | Jo Hsuan Fang, Jia Hong Jian, Ting Shen Kuo, Hsyueh Liang Wu, Hao Ching Chang, Way Zen Lee, Ping Yu Wu |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
chemistry.chemical_classification
Addition reaction Diene 010405 organic chemistry Aryl Organic Chemistry Enantioselective synthesis General Chemistry Tripeptide 010402 general chemistry 01 natural sciences Catalysis 0104 chemical sciences Amino acid chemistry.chemical_compound chemistry Organic chemistry Enantiomer |
| Zdroj: | Chemistry - A European Journal. 23:1830-1838 |
| ISSN: | 0947-6539 |
| DOI: | 10.1002/chem.201604120 |
| Popis: | An enantioselective RhI-catalyzed conjugate addition reaction of α-substituted β-nitroacrylates with various arylboronic acids by using chiral RhI diene catalysts is described for the first time. The addition reaction proceeds under mild conditions in a range of common organic solvents and additives, and it affords the corresponding quaternary-carbon-containing α,α-disubstituted β-nitropropionate products in up to 63 % yield and 99 % ee. Reaction of either (E)- or (Z)-β-nitroacrylates provided the same enantiomer of the product, and a range of esters and aryl groups were tolerated. To demonstrate the utility of the method, ethyl (R)-1,1-methyl-1-phenyl-3-nitropropionate, prepared herein, was converted to the non-proteinogenic β2,2-amino acid, (R)-2-(aminomethyl)-2-phenylpropanoic acid, and to the β2,2-lactam, (R)-3-methyl-3-phenylazetidin-2-one. In addition, a tripeptide, which comprised l-phenylalanine, l-alanine, and β2,2-amino acid 7, was also synthesized. |
| Databáze: | OpenAIRE |
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