Three-component organocascade kinetic resolution of racemic nitroallylic acetates via sequential iminium/enamine asymmetric catalysis

Suparna Roy, Kwunmin Chen

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

Nitroallylic acetates 1a-f have been kinetically resolved via an asymmetric three-component coupling that involves indoles, acrolein, and nitroolefin allylic acetates and is mediated by the chiral catalyst 2 (5 mol %). The reactions proceed via iminium/enamine cascade catalysis. Both recovered starting substrates and reaction products are typically obtained in high chemical yield and in good to excellent enantiopurity (79-95% ee for 1a-f and 83-99% ee for 3a-n). For the first time, a highly efficient three-component, organocascade kinetic resolution has been demonstrated.

Original languageEnglish
Pages (from-to)2496-2499
Number of pages4
JournalOrganic Letters
Volume14
Issue number10
DOIs
Publication statusPublished - 2012 May 18

Fingerprint

Catalysis
catalysis
acetates
Acetates
Acrolein
Indoles
Kinetics
indoles
kinetics
Reaction products
reaction products
cascades
catalysts
Catalysts
Substrates
products

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Three-component organocascade kinetic resolution of racemic nitroallylic acetates via sequential iminium/enamine asymmetric catalysis. / Roy, Suparna; Chen, Kwunmin.

In: Organic Letters, Vol. 14, No. 10, 18.05.2012, p. 2496-2499.

Research output: Contribution to journalArticle

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