Categories: C-C Bond Formation > Oxygen-, Nitrogen-containing molecules > Active methylenes >

1,4-addition of stabilized carbanions

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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.

A chiral strontium complex promotes the catalytic asymmetric Michael addition reactions of malonates to enones at room temperature, to afford the desired adducts in high yields and excellent enantioselectivities. This method provides an efficient approach to building blocks possessing various functional groups and possible sites for further functionalization.
M. Agostinho, S. Kobayashi, J. Am. Chem. Soc., 2008, 130, 2430-2431.

A 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.