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Complex Polycyclic Molecules from Acyclic Precursors via Transition Metal-Catalyzed Cascade Reactions

  • Corinne Aubert
  • Louis Fensterbank
  • Vincent Gandon
  • Max MalacriaEmail author
Chapter
Part of the Topics in Organometallic Chemistry book series (TOPORGAN, volume 19)

Abstract

This review gives an insight into the growing field of transition metal-catalyzed cascades. More particularly, we have focused on the construction of complex molecules from acyclic precursors. Several approaches have been devised. We have not covered palladium-mediated cyclizations, multiple Heck reactions, or ruthenium-catalyzed metathesis reactions because they are discussed in others chapters of this book. This manuscript is composed of two main parts. In the first part, we emphasize cascade sequences involving cycloaddition, cycloisomerization, or ene-type reactions. Most of these reaction sequences involve a transition metal-catalyzed step that is either followed by another reaction promoted by the same catalyst or by a purely thermal reaction. A simple change in the temperature of the reaction mixture is often the only technical requirement to go from one step to another. The second part covers the cascades relying on transition metalo carbenoid intermediates, which have recently undergone tremendous developments and synthetic applications. The first section deals with precursors already incorporating a carbenoid species (mostly diazo derivatives); the second section covers cascades in which an incipient carbenoid species originating from one or two catalytic steps intervenes.

Cascade Skeletal rearrangement Cycloisomerization Cycloaddition Carbenoid 

Abbreviations

Cp*

Pentamethylcyclopentadienyl

capH2

N-[(S)-3-Mercapto-2-methylpropionyl]-L-proline

DMAD

Dimethyl acetylenedicarboxylate

BPTV

N-Benzene-fused-phthalyl-(S)-valine

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Authors and Affiliations

  • Corinne Aubert
    • 1
  • Louis Fensterbank
    • 1
  • Vincent Gandon
    • 1
  • Max Malacria
    • 1
    Email author
  1. 1.Université Pierre et Marie CurieLaboratoire de Chimie Organique associé au CNRS Tour 44-54, 2ème étage, CC 229Paris Cedex 05France

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