Chiral Organocatalyzed Intermolecular Rauhut-Currier Reaction of Nitroalkenes with Ethyl Allenoate

Chem Pharm Bull (Tokyo). 2017;65(11):997-999. doi: 10.1248/cpb.c17-00554.

Abstract

An enantioselective intermolecular Rauhut-Currier (RC) reaction of nitroalkenes with ethyl allenoate has been established with quinidine-derived β-isocupreidine. The present RC reaction afforded α-functionalized allenoates 3 in up to 94% yield with 59% enantiomeric excess (ee).

Keywords: Rauhut–Currier reaction; chiral organocatalysis; nitroalkene; α-functionalized allenoate.

MeSH terms

  • Alkadienes / chemistry*
  • Alkenes / chemistry*
  • Catalysis
  • Cyclization
  • Esters / chemistry*
  • Molecular Structure
  • Nitro Compounds / chemistry*
  • Stereoisomerism

Substances

  • Alkadienes
  • Alkenes
  • Esters
  • Nitro Compounds