A New Method for Constructing Quaternary Carbon Centres: Tandem Rhodium-Catalysed 1,4-Addition/Intramolecular Cyclisation

A New Method for Constructing Quaternary Carbon Centres: Tandem Rhodium-Catalysed 1,4-Addition/Intramolecular Cyclisation

The efficient tandem rhodium‐catalysed 1,4‐addition/cyclisation of 1,1′‐alkenes using arylzinc chlorides is described. The simple one‐step synthesis of substituted cyclopentanone and cyclohexanone derivatives is performed from acyclic precursors using relatively low catalyst loadings under mild cond...

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Veröffentlicht in:Advanced synthesis & catalysis 2007-02, Vol.349 (3), p.432-440
Hauptverfasser: Le Nôtre, Jérôme, van Mele, David, Frost, Christopher G.
Format: Artikel
Sprache:eng
Schlagworte:
alkenes
conjugate addition
cyclisation
CC coupling
rhodium
zinc
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Zusammenfassung:The efficient tandem rhodium‐catalysed 1,4‐addition/cyclisation of 1,1′‐alkenes using arylzinc chlorides is described. The simple one‐step synthesis of substituted cyclopentanone and cyclohexanone derivatives is performed from acyclic precursors using relatively low catalyst loadings under mild conditions. A new quaternary carbon centre is created during the cyclisation step.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.200600355