NICKEL-CATALYZED CONJUGATE ADDITION OF TRIMETHYLALUMINUM TO STERICALLY HINDERED ALPHA,BETA-UNSATURATED KETONES

Authors
FLEMMING S KABBARA J NICKISCH K NEH H WESTERMANN J
Citation
S. Flemming et al., NICKEL-CATALYZED CONJUGATE ADDITION OF TRIMETHYLALUMINUM TO STERICALLY HINDERED ALPHA,BETA-UNSATURATED KETONES, Synthesis, (3), 1995, pp. 317-320
Citations number
56
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthesis → ACNP
ISSN journal
00397881
Issue
3
Year of publication
1995
Pages
317 - 320
Database
ISI
SICI code
0039-7881(1995):3<317:NCAOTT>2.0.ZU;2-Q
Abstract
Nickel acetylacetonate is an efficient catalyst for the 1,4-addition o f trimethylaluminum to alpha,beta-unsaturated ketones. The reaction is strongly solvent dependent and gives best results in tetrahydrofuran or ethyl acetate. The reaction is especially useful for the nucleophil ic 1,4-methyl transfer to sterically hindered enones. A beta-cuparenon e synthesis via conjugate methyl group addition to an enone precursor is described.