Kinetic Resolution of α-Nitrolactones by Catalytic Asymmetric Hydrolysis or Ester-Amide Exchange Reaction

Ryota Nakao, Yudai Fujii, Ichiro Hayakawa, Haruki Mizoguchi, Akira Sakakura

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

C1 -Symmetric chiral ammonium salt catalysts induced a kinetic resolution of racemic α-nitrolactones through an asymmetric ester-amide exchange reaction. The corresponding amides were obtained with high enantioselectivities and high S (= k fast / k slow) values. This reaction system is a useful approach for obtaining carbocyclic quaternary α-nitroamides as chiral building blocks.

Original languageEnglish
Pages (from-to)2018-2022
Number of pages5
JournalSynlett
Volume31
Issue number20
DOIs
Publication statusPublished - Dec 17 2020

Keywords

  • Bronsted acid catalysis
  • ester-amide exchange
  • hydrolysis
  • kinetic resolution
  • nitrolactones
  • quaternary amino acids

ASJC Scopus subject areas

  • Organic Chemistry

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