Categories: C-C Bond Formation > Oxygen-, Nitrogen-containing molecules > Active methylenes >
1,4-addition of stabilized carbanions
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Name Reactions
Recent Literature
The ionic liquid [bmIm]OH is a catalyst and a reaction medium for Michael
additions. Although the addition to α,β-unsaturated ketones gives the
monoaddition products, this ionic liquid always drives the reaction of
open-chain 1,3-dicarbonyl compounds with α,β-unsaturated esters and nitriles
toward bis-addition.
B. C. Ranu, S. Banerjee, Org. Lett., 2005,
7, 3049-3052.
Triphenylphosphine and tributylphosphine are excellent catalysts for Michael
additions of β-dicarbonyl compounds to electron-poor olefins, including
sterically demanding partners.
C. Gimbert, M. Lumbierres, C. Marchi, M. Moreno-Mañas, R. M. Sebastián, A.
Vallribera, Tetrahedron, 2005,
61, 8598-8605.
An intermolecular Michael addition of simple aldehydes to nonactivated
enones with high enantioselectivities is catalyzed by 5 mol-%
diphenylprolinol methyl ether.
Y. Chi, S. H. Gellman, Org. Lett.,
2005,
7, 4253-4256.
Highly enantioselective and effective Michael addition of diethyl malonate
to various chalcone derivatives has been achieved under mild phase-transfer
conditions using a chiral quaternary ammonium bromide as a catalyst.
T. Ooi, D. Ohara, K. Fukumoto, K. Maruoka, Org. Lett., 2005,
7, 3195-3197.
