Umpolung strategy: Advances in catalytic C-C bond formations

EYMUR S., GÖLLÜ M., TANYELİ C.

TURKISH JOURNAL OF CHEMISTRY, vol.37, no.4, pp.586-609, 2013 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 37 Issue: 4
  • Publication Date: 2013
  • Doi Number: 10.3906/kim-1303-85
  • Journal Name: TURKISH JOURNAL OF CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Page Numbers: pp.586-609
  • Keywords: Umpolung, thiamine pyrophosphate (TPP), N -heterocyclic carbene, asymmetric synthesis, INTERMOLECULAR STETTER REACTION, ACYL ANION EQUIVALENTS, ASYMMETRIC BENZOIN CONDENSATION, HETEROCYCLIC CARBENE CATALYSIS, CYANIDE ION, BENZOYLFORMATE DECARBOXYLASE, AROMATIC-ALDEHYDES, ENANTIOSELECTIVE SYNTHESIS, ACYLZIRCONOCENE CHLORIDE, NUCLEOPHILIC ACYLATION
  • Middle East Technical University Affiliated: Yes

Abstract

This mini-review examines the recent advances in umpolung strategy, devised originally by Corey and Seebach. Although numerous stoichiometric variants have been published to date, this article covers just the catalytic C-C bond forming reactions due to their major benefits such as atom economy, less pollution, and workable simplicity. In the context of umpolung, the studies are evaluated under 3 main titles: enzyme, N -heterocyclic carbene, and cyanide ion catalyzed reactions. In particular, enzyme and NHC catalyzed reactions mainly involve asymmetric applications.