Catalysis of Diazoalkane–Carbonyl Homologation. How New Developments in Hydrazone Oxidation Enable the Carbon Insertion Strategy for Synthesis

  • David C. Moebius
  • Victor L. Rendina
  • Jason S. Kingsbury
Chapter
First Online:
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 346)

Abstract

Diazo compounds continue both to challenge and to fascinate practitioners of chemical synthesis. The most strategically powerful and unique type of reactivity observed with these reagents is a formal insertion of the donor-acceptor carbon into C–C or C–H bonds alpha to carbonyl groups. Although the reaction does not involve discrete carbon–metal bonds, it can be catalyzed by metal-based Lewis acids. This chapter investigates both classical and modern developments in diazoalkyl carbon insertion with a special emphasis on nonstabilized nucleophiles.

Keywords

α-Functionalization C–C bond activation Carbon insertion Diazo compounds Scandium 
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Copyright information

© Springer-Verlag Berlin Heidelberg 2014

Authors and Affiliations

  • David C. Moebius
    • 1
  • Victor L. Rendina
    • 2
  • Jason S. Kingsbury
    • 3
  1. 1.Onyx Pharmaceuticals, Inc.South San FranciscoUSA
  2. 2.Pharmaceutical SciencesMassachusetts College of Pharmacy and Health SciencesBostonUSA
  3. 3.ChemistryCalifornia Lutheran UniversityThousand OaksUSA

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