Nickel-catalyzed conjugate addition of alkynyl groups to. alpha.,. beta.-unsaturated ketones
Document Type
Article
Publication Date
1980
Abstract
The complex formed by reaction of Ni (acac) 2 and DiBAH (1: 1) catalyzesconjugate addition of dialkylaluminum acetylides to, ß enones;; on hydrolysis, 3-alkynyl ketones are produced in high yield. Through this procedureconjugate addition of alkynyl groups to either S-cis or S-trans enones can be effected. This procedure is thefirst one which permits conjugate addition of terminal alkynyl units to ordinary S-trans enones. In cases wheremore than one stereochemical outcome is possible, conjugate addition of alkynyl units gives only one of these.Only 1,4-addition is observed and this only of the alkynyl unit. Complications arising from oxygen substitutionin the alkynyl side chain are described.
Recommended Citation
Schwartz, J., Carr, D. B., Hansen, R. T., & Dayrit, F. M. (1980). Nickel-catalyzed conjugate addition of alkynyl groups to. alpha.,. beta.-unsaturated ketones. The Journal of Organic Chemistry, 45(15), 3053-3061.
