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Updated: May 22, 2026

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Published on: February 7, 2019
Three-component organocascade kinetic resolution of racemic nitroallylic acetates via sequential iminium/enamine
1Department of Chemistry, National Taiwan Normal University, Taipei, Taiwan 116, ROC.
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.
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