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Synthesis 1995; 1995(3): 317-320
DOI: 10.1055/s-1995-3901
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Nickel-Catalysed Conjugate Addition of Trimethylaluminum to Sterically Hindered α,β-Unsaturated Ketones

Steffen Flemming* , Jazid Kabbara, Klaus Nickisch, Harribert Neh, Jürgen Westermann
  • *Schering AG, Pharma Process Research, Müllerstrasse 178, D-13342 Berlin, Germany
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Publikationsdatum:
31. Dezember 2000 (online)

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Nickel acetylacetonate is an efficient catalyst for the 1,4-addition of trimethylaluminum to α,β-unsaturated ketones. The reaction is strongly solvent dependent and gives best results in tetrahydrofuran or ethyl acetate. The reaction is especially useful for the nucleophilic 1,4-methyl transfer to sterically hindered enones. A β-cuparenone synthesis via conjugate methyl group addition to an enone precursor is described.

conjugate alkylation - trimethylaluminum - nickel catalysis - steric hindrance - (±)-β-cuparenone