Nucleophilic Addition-Electrophilic Coupling with a Carbanion Intermediate

X. Song, W. Wang

Research output: Chapter in Book/Report/Conference proceedingChapter


The strategy of nucleophilic addition-electrophilic couplings has become one of the central tenets and instruments in the arsenal of modern organic synthesis, since the discovery and development of novel catalytic systems and activation modes. In addition to traditional metal catalysis, organocatalysis has emerged as a new complementary tool, which has made significant achievements in the field. The broad selection of α,β-unsaturated compounds including α,β-unsaturated aldehydes, ketones, esters, amides, nitroolefins, and alkynals is presented, together with a variety of Michael donors and carbophilic electrophiles have been conceived and harvested for the efficient and stereoselective construction of complex molecular architectures, which usually possess at least two chiral centers. The approach can dramatically improve the synthetic efficiency in a fashion of the atom economy, and naturally falls into the category of a cascade reaction.

Original languageEnglish (US)
Title of host publicationAdditions to and Substitutions at C-C π-Bonds
PublisherElsevier Ltd.
Number of pages33
ISBN (Print)9780080977430
StatePublished - Feb 2014
Externally publishedYes


  • Asymmetric catalysis
  • Cascade reaction
  • Electrophilic coupling
  • Metal catalyst
  • Michael addition
  • Nucleophilic addition
  • Organocatalyst
  • α,β-Unsaturated compounds

ASJC Scopus subject areas

  • General Chemical Engineering
  • General Chemistry


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