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.

A highly enantioselective Michael addition of malonates to α,β-unsaturated
ketones in water is catalyzed by a primary-secondary diamine catalyst containing
a long alkyl chain. This asymmetric Michael addition process allows the
conversion of various α,β-unsaturated ketones.
Z. Mao, Y. Jia, W. Li, R. Wang, J. Org. Chem., 2010,
75, 7428-7430.

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.

Various bis-activated cyclopropenes undergo highly stereoselective ring-opening
reactions to produce multisubstituted alkenyl halides in the presence of
stoichiometric magnesium halides. Trapping of the magnesium enolate
intermediates in situ allows the synthesis of highly functionalized compounds.
Y. Wang, H. W. Lam, J. Org. Chem., 2009,
74, 1353-1355.


