1206-21-9Relevant academic research and scientific papers
Building Congested Ketone: Substituted Hantzsch Ester and Nitrile as Alkylation Reagents in Photoredox Catalysis
Chen, Wenxin,Liu, Zheng,Tian, Jiaqi,Li, Jin,Ma, Jing,Cheng, Xu,Li, Guigen
supporting information, p. 12312 - 12315 (2016/10/07)
For the first time, 4-alkyl Hantzsch esters were used to construct molecules with all-carbon quaternary centers by visible light-induced photoredox catalysis via transfer alkylation. Up to a 1500 h-1 turnover frequency was achieved in this reaction. Reactions of 4-alkyl Hantzsch nitriles as tertiary radical donors joined two contiguous all-carbon quaternary centers intermolecularly, and this chemistry was used to synthesize a common precursor of a class of hydroxysteroid dehydrogenase inhibitors.
Palladium-catalyzed cross-coupling of cyclopropanols with aryl halides under mild conditions
Rosa, David,Orellana, Arturo
, p. 110 - 113 (2011/03/22)
Intra- and intermolecular palladium-catalyzed cross-coupling of cyclopropanols with aryl halides can be achieved in good yields under mild conditions.
Lithium naphthalenide induced reductive alkylation of α-cyano ketones. A general method for regiocontrol of α,α-dialkylation of ketones
Liu, Hsing-Jang,Zhu, Jia-Liang,Shia, Kak-Shan
, p. 4183 - 4186 (2007/10/03)
An efficient general method for the consecutive introduction of two alkyl groups to the α carbon of a ketone carbonyl has been developed, making use of the lithium naphthalenide induced reductive alkylation of an α-cyano ketone system as a key operation.
Highly regioselective alkylation at the more hindered α-site of unsymmetrical ketones by use of their potassium enolates. A comparative study with lithium enolates
Quesnel, Yannick,Bidois-Sery, Laure,Poirier, Jean-Marie,Duhamel, Lucette
, p. 413 - 415 (2007/10/03)
Alkylation of regioisomeric potassium enolates 4 and 6 obtained from corresponding silyl enol ethers 2 and 3 occurs at the most substituted site affording ketones 8. Alkylation of corresponding lithium enolates 5 and 7 occurs at the expected site affording ketones 8 or 9. As an application the one pot synthesis of spiroketones 13 from silyl enol ethers 12 is described.
Highly Regioselective Monoalkylation of Ketones via Manganese Enolates. Prepared from Lithium Enolates
Cahiez, Gerard,Chau, Khi,Clery, Patrick
, p. 3069 - 3072 (2007/10/02)
Li-enolates are readily converted to Mn-enolates by treatment with manganese halides.In THF, the reaction is easily and economically performed with manganese chloride at room temperature.Mn-enolates can then be regioselectively monoalkylated in good yields.The formation of di and polyalkylated products is never observed (1percent).
Dependence of the Lewis Acid-Induced Reaction of β-Stannyl Ketones upon Substitution Pattern: Cyclopropanation versus 1,2-Alkyl Migration
Fujiwara, Jun,Sato, Tadashi
, p. 1258 - 1264 (2007/10/02)
3-Stannylcyclohexanones fully substituted at 2 and 3 positions underwent a 1,2-aklyl migration, along with the cyclopropanation.The balance of the reactions depended upon the steric environment and migratory aptitude of the alkyl groups.
ALKYLATION DIRECTE DE CETONES ET D'ALDEHYDES EN PRESENCE DE POTASSE SOLIDE EN SUSPENSION
Artaud, I.,Torossian, G.,Viout, P.
, p. 5031 - 5038 (2007/10/02)
Dehydrated solid KOH, suspended in aprotic solvents, is used as a base for ketone and aldehyde alkylation.The best solvent as regards yields and selectivity is DME.The quantity of KOH depends on the carbonyl compound acidity.This method gives as good results as less convenient homogeneous conditions.
Tris(dialkylamino)sulfonium Enolates. Synthesis, Structure, and Reactions
Noyori, R.,Nishida, I.,Sakata, J.
, p. 1598 - 1608 (2007/10/02)
A mixture of an enol trimethylsilyl ether and a fluoride salt exists in a dynamic equilibrium with an enolate species and fluorotrimethylsilane.Evacuation of an equimolar mixture of an enol trimethylsilyl ether of benzyl methyl ketone and tris(diethylamino)sulfonium (TAS) difluorotrimethylsiliconate produces fluorotrimethylsilane as the volatile fraction and the corresponding TAS enolate as air-sensitive crystals.The conductivity measurement and the 1H and 13C NMR analysis have substantiated the ionic nature of the TAS enolate in THF.The NMR chemical shifts are interpreted in terms of the electron distribution.The isolated TAS enolate undergoes O-acetylation with acetic anhydride and C-alkylation with methyl iodide exclusively.TAS enolate intermediates generated in situ from a series of enol silyl ethers and TAS difluorotrimethylsiliconate react with various active organic halides under mild conditions to give the regiospecific C-alkylation products.The in situ formed enolates react with aldehyde substrates to afford the β-trimethylsiloxy ketone adducts.In most cases, the reaction is kinetically controlled and the major products have erythro stereochemistry regardless of enolate configuration.This aldol reaction is postulated to proceed via an acyclic, extended transition state, in contrast to ordinary aldol reactions of Lewis acid coordinated enolates, which take place by way of six-membered chelate transition states.
