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α‐Olefins as Alkenylmetal Equivalents in Catalytic Conjugate Addition Reactions
Author(s) -
Ho ChunYu,
Ohmiya Hirohisa,
Jamison Timothy F.
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200705163
Subject(s) - trifluoromethanesulfonate , chemistry , alkene , conjugate , stereoselectivity , reagent , amine gas treating , silylation , phosphine , aryl , yield (engineering) , allene , catalysis , base (topology) , ethylene , organic chemistry , medicinal chemistry , combinatorial chemistry , alkyl , mathematical analysis , materials science , mathematics , metallurgy
In the presence of a silyl triflate and an amine base, a nickel–phosphine complex catalyzes the direct conjugate addition of ethylene, α‐olefins, and aryl alkenes to unsaturated aldehydes and ketones. The enolsilane products are isolated in good to very high yield, and in very high stereoselectivity for some cases. The alkene is a functional equivalent of an alkenylmetal reagent in the transformation.