Categories: C-C Bond Formation > Oxygen-containing molecules > α,β-unsaturated compounds >
Synthesis of enones
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Synthesis of
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Recent Literature
α-Haloalkenyl acetals react smoothly with (het)aryl boronic acids, aryl
boronates, or B-alkyl-9-borabicyclo[3.3.1]nonanes through Pd-catalyzed
Suzuki cross-coupling in very good yields. This mild protocol features a broad
substrate scope and good functional-group compatibility, and is easily scaled
up.
L. Zhang, Synlett, 2021, 32,
723-727.
Morita-Baylis-Hillman Reaction of α,β-Unsaturated Ketones with Allylic
Acetates by the Combination of Transition-Metal Catalysis and Organomediation
Y.-Q. Li, H.-J. Wang, Z.-Z. Huang, J. Org. Chem.,
2016,
81, 4429-4433.
An alkyl intercepted Meyer-Schuster rearrangement with α,β-unsaturated
ketones as the electrophiles conveniently provided
2-methylene-pentane-1,5-diones in high yields. An optional in situ Michael
addition of malononitrile gives diverse 2-malononitrile methyl substituted
pentane-1,5-diones.
Z. Wang, Y. Sun, Q. Zhang, W. Pan, T. Li, Y. Yin, J. Org. Chem., 2022, 87,
3329-3340.
Using a catalytic amount of trialkylphosphines, alkyl halides undergo
efficient intramolecular Morita-Baylis-Hillman cyclization.
M. E. Krafft, K. A. Seibert, Synlett, 2006,
3334-3336.
An organomediated, intramolecular Morita-Baylis-Hillman reaction of
molecules bearing allylic leaving groups as the electrophilic partner
provided a facile, high yielding, straightforward synthesis of densely
functionalized cyclic molecules.
M. E. Krafft, T. F. N. Haxell, J. Am. Chem. Soc.,
2005,
127, 10168-10169.
An efficient cycloallylation of mono-enone mono-allylic carbonates is
achieved upon exposure to tributylphosphine and 1 mol % Pd(Ph3P)4.
This transformation combines the nucleophilic features of the
Morita-Baylis-Hillman reaction with the electrophilic features of the
Trost-Tsuji reaction.
B. G. Jellerich, J.-R. Kong, M. J. Krische, J. Am. Chem. Soc.,
2003,
125, 7758-7759.