In 2022,Yesilcimen, Ahmet; Jiang, Na-Chuan; Gottlieb, Felix H.; Wasa, Masayuki published an article in Journal of the American Chemical Society. The title of the article was 《Enantioselective Organocopper-Catalyzed Hetero Diels-Alder Reaction through in Situ Oxidation of Ethers into Enol Ethers》.Application In Synthesis of Ethyl oxalyl monochloride The author mentioned the following in the article:
A catalytic method for the enantio- and diastereoselective union of alkyl ethers R1CH2CH2OR2 (R1 = H, CH2Si(Me)3, Ph, 1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl, etc.; R2 = CH3, CD3) and heterodienes R3CH=CHC(O)C(O)OR4 (R3 = Me, Ph, 4-bromophenyl, 4-methoxy Ph, 1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl ; R4 = Et, prop-2-en-1-yl) was disclosed. A chiral Cu-BOX complex that catalyzes the efficient oxidation of ethers into enol ethers in the presence of trityl acetate has been demonstrated. Then, the organocopper promotes stereoselective hetero Diels-Alder reaction between the in situ generated enol ethers and β,β-unsaturated ketoesters, allowing for rapid access to an array of dihydropyran derivatives endo/exo I and II possessing three vicinal stereogenic centers. In the experiment, the researchers used many compounds, for example, Ethyl oxalyl monochloride(cas: 4755-77-5Application In Synthesis of Ethyl oxalyl monochloride)
Ethyl oxalyl monochloride(cas: 4755-77-5) belongs to acyl chlorides. In the laboratory, acyl chlorides are generally prepared by treating carboxylic acids with thionyl chloride (SOCl2). The reaction is catalyzed by dimethylformamide and other additives.Application In Synthesis of Ethyl oxalyl monochloride
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