Synthesis of Quaternary-Carbon-Containing β2,2-Amino Acids by the RhI-Catalyzed Enantioselective Arylation of α-Substituted β-Nitroacrylates

Jo Hsuan Fang, Jia Hong Jian, Hao Ching Chang, Ting Shen Kuo, Way Zen Lee, Ping Yu Wu, Hsyueh Liang Wu

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)1830-1838
Number of pages9
JournalChemistry - A European Journal
Volume23
Issue number8
DOIs
Publication statusPublished - 2017 Jan 1

Keywords

  • amino acids
  • asymmetric catalysis
  • conjugate addition
  • diene ligands
  • rhodium

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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