Categories: C-C Bond Formation > Oxygen-, Nitrogen-containing molecules > Active methylenes >
Alkenylations
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Recent Literature
α-Vinylated ketoester are atom-economically produced by an In(OTf)3-catalyzed
addition of β-ketoesters to welding-grade acetylene in the presence of molecular
sieves under solvent-free conditions in good to excellent yield.
M. Nakamura, K. Endo, E. Nakamura, Org. Lett., 2005,
7, 3279-3281.
1,3-Dicarbonyl compounds add to unactivated alkynes in the presence of less than
1 mol-% of indium(III) trifluoromethanesulfonate in high to excellent yield to
give 2-alkenylated 1,3-dicarbonyl compounds. This mild reaction does not require
solvent and tolerates various functional groups.
K. Endo, T. Hatakeyama, M. Nakamura, E. Nakamura, J. Am. Chem. Soc., 2007,
129, 5264-5271.
The Bu3P-catalyzed addition of 1,3-diketones, β-keto esters and
malonates to alkynoates allows an improved, mild and efficient one pot access to
α-(gem-difunctional) cinnamate esters and to conjugated 1,3-diketones.
M. Hanédanian, O. Loreau, M. Sawicki, F. Taran, Tetrahedron, 2005,
61, 2287-2294.
[ReBr(CO)3(thf)]2 catalyzed the reactions of
1,3-dicarbonyl compounds with terminal acetylenes, which gave the corresponding
alkenyl derivatives in excellent yields.
Y. Kuninobu, A. Kawata, K. Takai, Org. Lett.,
2005,
7, 4823-4825.
Y. Kuninobu, A. Kawata, K. Takai, Org. Lett.,
2005,
7, 4823-4825.
A Ni(II)-catalyzed Conia-ene reaction of various acetylenic
1,3-dicarbonyl compounds has been discovered. The reaction gave mono- and
bicyclic olefinic cyclopentantes in good yields in the presence of Ni(acac)2
and Yb(OTf)3.
Q. Gao, B.-F. Zheng, J.-H. Li, D. Yang, Org. Lett., 2005,
7, 2185-2188.
An organocatalytic highly enantioselective formation of vinyl-substituted
all-carbon quaternary stereocenters proceeds in good yield via nucleophilic
vinylic substitution of various α-substituted-α-cyanoacetates with
α-chloroalkenones using a dimeric cinchona alkaloid phase-transfer catalyst.
M. Bell, T. B. Poulsen, K. A. Jørgensen, J. Org. Chem., 2007,
72, 3053-3056.
