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The Virtue of Michael-Type Addition Processes in the Design of Transition Metal-Promoted Cyclizative Cascade Reactions

  • Geneviève BalmeEmail author
  • Didier Bouyssi
  • Nuno Monteiro
Chapter
Part of the Topics in Organometallic Chemistry book series (TOPORGAN, volume 19)

Abstract

Cascade reactions involving a transition metal-promoted step and a Michael-type addition process have emerged as a powerful tool to construct cyclic and polycyclic structures. In this review, recent advances in this field are presented. The first part is related to cycloaddition reactions based on zwitterionic C − C-allylPd complexes. The second part deals with Michael initiated metal-catalyzed cyclofunctionalization reactions of unactivated C − C ′-bonds . Parts three and four feature reactions where an initial Michael addition reaction is followed by either a coupling reaction or an electrophilic trapping. Part five is devoted to Michael terminated reactions.

Cyclization Heterocycles Michael addition Tandem reactions Transition metal catalysis 

Abbreviations

BINAP

2,2′-bis(diphenylphosphino)-1,1′-binaphtyl

COD

cyclooctadiene

dba

dibenzylidene acetone

DCM

dichloromethane

DME

dimethoxyethane

DMF

dimethylformamide

DMSO

dimethylsulfoxide

dppb

1,4-bis(diphenylphosphino)butane

dppe

1,2-bis(diphenylphosphino)ethane

dppp

1,3-bis(diphenylphosphino)propane

EWG

electron-withdrawing group

L

ligand

MCP

methylene cyclopropane

MS

3 Å molecular sieves 3 Å

Nu

nucleophile

THF

tetrahydrofuran

TMM

trimethylene methane

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Authors and Affiliations

  • Geneviève Balme
    • 1
    Email author
  • Didier Bouyssi
    • 1
  • Nuno Monteiro
    • 1
  1. 1.Laboratoire de Chimie OrganiqueCNRS UMR 5181, Université Claude Bernard Lyon 1Villeurbanne CedexFrance

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