Nickel-catalyzed conjugate addition of alkynyl groups to. alpha.,. beta.-unsaturated ketones

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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.