Categories: C-C Bond Formation > Oxygen-containing molecules > Carbonyl compounds >
Synthesis of allyl ketones and aldehydes
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Name Reactions
Recent Literature
A selective coupling of alkynylsilanes and allyltrimethylsilane is catalyzed
by 5 mol% of indium tribromide under mild conditions to afford the
corresponding α,β-acetylenic ketones and β,γ-unsaturated ketones in
excellent yields.
J. S. Yadav, B. V. S. Reddy, M. Sridhar Reddy, G. Parimala, Synthesis,
2003, 2390-2394.
Under the conditions of ruthenium-catalyzed transfer hydrogenation, 1,3-dienes
couple to benzylic and aliphatic alcohols and aldehydes to deliver
β,γ-unsaturated ketones in very good yields. In all cases, complete branch
regioselectivity is observed.
F. Shibahara, J. F. Bower, M. J. Krische, J. Am. Chem. Soc., 2008,
130, 14120-14122.
F. Shibahara, J. F. Bower, M. J. Krische, J. Am. Chem. Soc., 2008,
130, 14120-14122.
An efficient cross-addition reaction of dienes with aldehydes in the presence of
RuHCl(CO)(PPh3)3 as catalyst gives various β,γ-unsaturated
ketones. A π-allylruthenium species, derived from hydroruthenation of the diene,
may be involved as a key intermediate.
S. Omura, T. Fukuyama, J. Horiguchi, Y. Murakami, I. Ryu, J. Am. Chem. Soc., 2008,
130, 14094-14095.
