Download PDF
Synthesis 1995; 1995(3): 317-320
DOI: 10.1055/s-1995-3901
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

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