Enantioselective Conjugate Addition and 1,2-Addition to C=N of Organolithium Reagents

  • Mayu Iguchi
  • Ken-ichi Yamada
  • Kiyoshi Tomioka
Part of the Topics in Organometallic Chemistry book series (TOPORGAN, volume 5)


Organolithium reagents are highly reactive species and are used in a variety of organic transformations. Development of new methodology for asymmetric reactions of organolithium reagents constitutes a remarkable area of fundamental progresses in recent synthetic organic chemistry. The conjugate addition (or Michael reaction, 1,4-addition) and 1,2-addition to C= N double bonds are powerful methods for forming a carbon-carbon bond. This chapter reviews the recent progress in enantioselective conjugate addition and 1,2-addition to C=N double bonds by organolithium reagents. Sect. 1 considers conjugate addition reactions with activated olefins and α,β-unsaturated imines, focusing on reactions controlled by external chiral ligands. Chiral oxazoline chemistry is also briefly presented. Sect. 2 summarizes the 1,2-additions to imines and imine congeners (hydrazones, oxime ethers, nitrones) using chiral auxiliaries and chiral ligands. We do not describe additions which use chiral auxiliary groups in carbonyl compounds.


Asymmetric reaction Organolithium Conjugate addition Imine Chiral ligand 


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Copyright information

© Springer-Verlag Berlin Heidelberg 2003

Authors and Affiliations

  • Mayu Iguchi
    • 1
  • Ken-ichi Yamada
    • 1
  • Kiyoshi Tomioka
    • 1
  1. 1.Graduate School of Pharmaceutical SciencesKyoto UniversityKyotoJapan

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