摘要
An enantioselective RhI-catalyzed conjugate addition reaction of α-substituted β-nitroacrylates with various arylboronic acids by using chiral RhIdiene 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.
原文 | 英語 |
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頁(從 - 到) | 1830-1838 |
頁數 | 9 |
期刊 | Chemistry - A European Journal |
卷 | 23 |
發行號 | 8 |
DOIs | |
出版狀態 | 已發佈 - 2017 2月 3 |
ASJC Scopus subject areas
- 催化
- 有機化學
指紋
深入研究「Synthesis of Quaternary-Carbon-Containing β2,2-Amino Acids by the RhI-Catalyzed Enantioselective Arylation of α-Substituted β-Nitroacrylates」主題。共同形成了獨特的指紋。資料集
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CCDC 1942678: Experimental Crystal Structure Determination
Fang, J. (Contributor), Jian, J. (Contributor), Chang, H. (Contributor), Kuo, T. (Contributor), Lee, W. (Contributor), Wu, P. (Contributor) & Wu, H. (Contributor), Unknown Publisher, 2019
DOI: 10.5517/ccdc.csd.cc236j1x, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc236j1x&sid=DataCite
資料集: Dataset