Crossed intramolecular Rauhut-Currier-type reactions via dienamine activation

Org Lett. 2009 Sep 17;11(18):4116-9. doi: 10.1021/ol901614t.

Abstract

The intramolecular Rauhut-Currier reaction creates a carbon-carbon bond between two tethered Michael acceptors. Previous asymmetric versions have relied on 1,4-additions of chiral nucleophilic catalysts. Herein, we investigate a novel strategy that involves the formation of electron rich dienamines as key intermediates. Our methodology provides an efficient entry to the iridoid framework.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbon / chemistry*
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Cross Reactions
  • Crystallography, X-Ray / methods
  • Cyclization
  • Hydrogen Peroxide / chemistry
  • Molecular Structure
  • Oxygen / chemistry*
  • Oxygen / classification
  • Stereoisomerism

Substances

  • Carbon
  • Hydrogen Peroxide
  • Oxygen