76638-59-0Relevant academic research and scientific papers
C-acylation of enolates from lithium dimethylcuprate addition to α,β-unsaturated ketones
Bernasconi,Gariboldi,Jommi,Sisti
, p. 2337 - 2340 (1980)
The enolates from 1,4 addition of lithium dimethylcuprate to 2-cyclohexenone, 2-cyclopentenone and methyl vinyl ketone, with acetyl chloride, give only C-acylated products and not O-acylated products as previously reported in literature.
TRAPPING REACTION OF ENOLATES FROM LITHIUM DIMETHYLCUPRATE CONJUGATED ADDITION: IMPORTANCE OF STERIC FACTORS AND, PARTICULARLY, OF β-SUBSTITUTION OF ENONE IN THE C- vs. O-ACYLATION
Bernasconi, Silvana,Jommi, Giancarlo,Montanari, Stefania,Sisti, Massimo
, p. 125 - 128 (2007/10/02)
Conjugated addition of lithium dimethylcuprate to α,β-unsaturated ketones gives intermediate enolates which, treated with acetyl chloride, undergo O- and/or C-acylation depending on the substitution at the enone β-carbon.Results agree with the hypothesis that C-acylation proceeds through an intramolecular metal-assisted mechanism.
