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- Title
Synthesis of Quaternary-Carbon-Containing β<sup>2,2</sup>-Amino Acids by the Rh<sup>I</sup>-Catalyzed Enantioselective Arylation of α-Substituted β-Nitroacrylates.
- Authors
Fang, Jo ‐ Hsuan; Jian, Jia ‐ Hong; Chang, Hao ‐ Ching; Kuo, Ting ‐ Shen; Lee, Way ‐ Zen; Wu, Ping ‐ Yu; Wu, Hsyueh ‐ Liang
- Abstract
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.
- Subjects
RHODIUM catalysts; AMINO acid synthesis; SUBSTITUENTS (Chemistry); ACRYLATES; ARYLATION; ORGANIC solvents
- Publication
Chemistry - A European Journal, 2017, Vol 23, Issue 8, p1830
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201604120