Issue 6, 2024

Catalytic asymmetric ring-opening of aminocyclopropanes with oxygen nucleophiles: access to chiral γ-amino acid derivatives

Abstract

Donor–acceptor aminocyclopropanes containing both amino and carboxyl groups underwent efficient catalytic asymmetric ring-opening reactions with diverse oxygen nucleophiles to afford chiral γ-oxygen-substituted γ-aminobutyric acid derivatives in 60–96% yields and 70–99% ee. With imidazoline-pyrroloimidazolone pyridine as the chiral ligand, a broad range of oxygen nucleophiles, including alcohols, phenols, carboxylic acids, 4-hydroxycoumarins and 1,3-cyclodiones are compatible. The developed method was applied to the derivatization of complex molecules including (−)-myrtenol, stavudine, (S)-naproxen, and (−)-estrone.

Graphical abstract: Catalytic asymmetric ring-opening of aminocyclopropanes with oxygen nucleophiles: access to chiral γ-amino acid derivatives

Supplementary files

Article information

Article type
Research Article
Submitted
09 Dec 2023
Accepted
01 Feb 2024
First published
01 Feb 2024

Org. Chem. Front., 2024,11, 1817-1823

Catalytic asymmetric ring-opening of aminocyclopropanes with oxygen nucleophiles: access to chiral γ-amino acid derivatives

R. Luo, X. Wang, M. Xie and H. Guo, Org. Chem. Front., 2024, 11, 1817 DOI: 10.1039/D3QO02036C

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