Palladium-Catalyzed Asymmetric Allylic Alkylation of 4-Substituted Isoxazolidin-5-ones: Straightforward Access to β2,2 -Amino Acids

Chemistry. 2018 Apr 3;24(19):4810-4814. doi: 10.1002/chem.201800641. Epub 2018 Mar 13.

Abstract

We report here an unprecedented and highly enantioselective palladium-catalyzed allylic alkylation applied to 4-substituted isoxazolidin-5-ones. Ultimately, the process provides a straightforward access to β2,2 -amino acids bearing an all-carbon quaternary stereogenic center in great yields and a high degree of enantioselectivity.

Keywords: allylic alkylation; asymmetric catalysis; beta-lactams; beta2,2-amino acids; isoxazolidinones; palladium.

MeSH terms

  • Alkylation
  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry
  • Amino Acids, Basic
  • Catalysis
  • Isoxazoles / chemistry*
  • Palladium / chemistry*
  • Stereoisomerism

Substances

  • Amino Acids
  • Amino Acids, Basic
  • Isoxazoles
  • Palladium