36971-09-2Relevant academic research and scientific papers
Synthesis of Enones and Enals via Dehydrogenation of Saturated Ketones and Aldehydes
Pan, Gao-Fei,Zhu, Xue-Qing,Guo, Rui-Li,Gao, Ya-Ru,Wang, Yong-Qiang
, p. 4774 - 4783 (2018/11/10)
A general, efficient and economic palladium-catalyzed dehydrogenation to form enones or enals has been developed. The approach possesses extremely broad substrate scope including various linear or cyclic saturated ketones and aldehydes. The protocol is ligand-free, and molecular oxygen is used as the sole clean oxidant in the reaction. Due to mild reaction conditions, good functional group compatibility, and versatile utilities of enones and enals, the method can be applied in the late-stage synthesis of natural products, pharmaceuticals and fine chemicals. (Figure presented.).
Facile synthesis of dihydrochalcones via the AlCl3-promoted tandem Friedel-Crafts acylation and alkylation of arenes with 2-alkenoyl chlorides
Zhou, Yang,Li, Xinyao,Hou, Shili,Xu, Jiaxi
, p. 203 - 211 (2013/01/14)
Tandem Friedel-Crafts acylation and alkylation of arenes with 2-alkenoyl chlorides were investigated under the catalysis of Lewis acids. The cascade reaction affords dihydrochalcones in good yields accompanying 1-indanone derivatives in some cases, in the presence of anhydrous aluminum chloride. The scope, limitation, and mechanism of the tandem reaction were also explored. The intermolecular Friedel-Crafts alkylation for the formation of dihydrochalcones is more favorable than the intramolecular one for the generation of 1-indanones in the tandem reaction due to a stable six-membered ring transition state. The sequent process was further studied by the DFT computations at the M06-2X/6-31G(d) level, which are in great agreement with the experimental observation and support the proposed mechanism. The current method provides a convenient and economic method to synthesis of dihydrochalcones.
Can simple enones be useful partners for the catalytic stereoselective alkylation of indoles?
Bandini, Marco,Fagioli, Matteo,Garavelli, Marco,Melloni, Alfonso,Trigari, Valerio,Umani-Ronchi, Achille
, p. 7511 - 7518 (2007/10/03)
A new catalytic system for the first example of enantioselective Friedel-Crafts-type (FC) addition of indoles to simple enones is described. The use of an equimolar amount of chiral [Al(salen)Cl] and 2,6-lutidine (10 mol%) was found to be effective in pro
Stereochemistry of the Michael Addition of N,N-Disubstituted Amide and Thioamide Enolates to α,β-Unsaturated Ketones
Oare, David A.,Henderson, Mark A.,Sanner, Mark A.,Heathcock, Clayton H.
, p. 132 - 157 (2007/10/02)
A systematic study of the regio- and diastereoselectivity of the kinetic Michael addition of amide and thioamide enolates to a series of α,β-unsaturated ketones has been carried out.Factors that influence the diastereo- and regiochemical outcome of the reaction include the substitution pattern of the enone and enolate, the enolate counterion, and the solvent.Numerous examples of high selectivity have been discovered.In a number of examples, either the syn or the anti addition products can be obtained by varying the nature of the solvent, donor atom, and/or counterion.These results have correlated in terms of a coherent transition-state model.
