Synthesis of enones
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.
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.