52784-38-0Relevant articles and documents
Asymmetric Domino Reaction of α,β-Unsaturated Aldehydes and α-Acyl α,β-Unsaturated Cyclic Ketones Catalyzed by Diphenylprolinol Silyl Ether
Hayashi, Yujiro,Suga, Yurina,Umekubo, Nariyoshi
supporting information, (2020/11/18)
An asymmetric domino reaction combining vinylogous Michael reaction, hydration of aldehyde, and oxy-Michael reaction proceeds with α,β-unsaturated aldehydes and α-acyl α,β-unsaturated cyclic ketones in the presence of diphenylprolinol silyl ether to afford tetrahydrochromane derivatives with excellent enantioselectivity. After the domino reaction, addition of Wittig reagent and acid in the same reaction vessel promoted a second domino reaction incorporating retro oxy-Michael reaction, isomerization, and Wittig reaction to afford chiral functionalized cyclic 1,3-diene derivatives with excellent enantioselectivity. Overall, six reaction steps proceed in a one-pot procedure.
An efficient and mild oxidation of α-isophorone to ketoisophorone catalyzed by N-hydroxyphthalimide and copper chloride
Chen, Lihua,Tang, Ruiren,Li, Zhongying,Liang, Shan
experimental part, p. 459 - 463 (2012/05/20)
N-hydroxyphthalimide (NHPI) and copper chloride (CuCl2) were first utilized for aerobic oxidation of α-isophorone (α-IP) to ketoisophorone (KIP) and the effects of co-catalysts, temperature, reaction time, solvent, amount of CuCl2 and pressure of oxygen were investigated extensively. NHPI/CuCl2 turned out to be highly efficient to this oxidation with up to 91.3% conversion and 81.0% selectivity under mild conditions. And various hydrocarbons including benzylic compounds, cycloalkene and its derivatives were also oxidized smoothly under optimized conditions. Moreover, the possible reaction mechanism was proposed and verified by FT-IR spectra.
Use of a Sacrificial Aluminum Anode in the Acylation of Some Olefins
Vukicevic, Rastko D.,Joksovic, Ljubinka,Konstantinovic, Stanimir,Markovic, Zoran,Mihailovic, Mihailo Lj.
, p. 899 - 904 (2007/10/03)
The acylation of some alicyclic and aliphatic alkenes by the electrochemical generation of a catalyst using a sacrificial aluminum anode was investigated. Substrates were electrolyzed in a dichloromethane solution of an appropriate electrolyte (tetraalkylammonium salts) in the presence of an acylating agent (acetyl chloride or anhydride). Thus, unsubstituted cycloalkenes, namely cyclohexene and cycloheptene, gave by that reaction conjugated ketones, i.e. the corresponding 1-acetylcycloalkenes, as the only unsaturated carbonyl compounds in moderate-to-good yields. Under the same reaction conditions their 1-methyl derivatives gave mixtures of the corresponding conjugated and β,γ-unsaturated isomeric ketones in which unconjugated compounds predominate. In both cases unsaturated ketones were accompanied by different amounts of side products. Terminal aliphatic alkenes (1-hexene, 1-heptene, and 1-dodecene) afforded only conjugated a ketone with a normal skeleton, but in lower yields. The acylation of cyclohexene was studied in more detail, altering the reaction conditions by changing the reaction temperature, the supporting electrolyte, the acylating agent and the electrochemical cell. Mechanistic considerations were made on the basis of the products distribution and some theoretical calculations being made by the MOPAC program package (version 7.0).
