1077-59-4Relevant academic research and scientific papers
Ruthenium-Catalyzed Enantioselective Hydrogenation/Lactonization of 2-Acylarylcarboxylates: Direct Access to Chiral 3-Substituted Phthalides
Lu, Bin,Zhao, Mengmeng,Ding, Guangni,Xie, Xiaomin,Jiang, Lili,Ratovelomanana-Vidal, Virginie,Zhang, Zhaoguo
, p. 3989 - 3996 (2017/09/13)
Highly enantioselective tandem hydrogenation/lactonization of various 2-acylarylcarboxylates including 2-aroylarylcarboxylates were realized by using [RuCl(benzene)(S)-SunPhos]Cl as the catalyst under mild reaction conditions. Excellent enantioselectivities (up to 99.6 % ee) and activities (S/C=1000) were obtained. This convenient and practical method enables a direct access to a series of highly optically pure 3-substituted phthalides that are very important molecules as valuable pharmacological compounds and diversified synthons for medicinal chemistry. Moreover, a gram-scale reaction was performed to further demonstrate the practicality of this approach.
Preparation and cycloaddition reactions of novel heterocyclic mesomeric betaines
Morgan, David O.,David Ollis,Stanforth, Stephen P.
, p. 5523 - 5534 (2007/10/03)
The heterocyclic mesomeric betaines 6a-c reacted with dimethyl acetylenedicarboxylate and ethyl propiolate giving the 1,3-dipolar cycloaddition products 7a-c and 8a-c, respectively. With esters of maleic, fumaric, acrylic and methacrylic acids, mesomeric betaines 6a and 6b gave substituted tetralone derivatives. (C) 2000 Elsevier Science Ltd.
Reactions of Carbonyl Compounds in Basic Solutions. Part 10. Methoxide-catalysed Cyclization of Methyl 2-Acylbenzoates and 8-Acyl-1-naphthoates
Bowden, Keith,Chehel-Amiran, Mohsen
, p. 2035 - 2038 (2007/10/02)
The detailed mechanism of the methoxide-catalysed rearrangement of both normal and pseudo methyl o-acylbenzoates and 8-acyl-1-naphthoates to form indane-1,3-diones and phenalene-1,3-diones, respectively, has been studied.Rate-acidity function correlations for the reactions in methanolic dimethyl sulphoxide give linear relations.The kinetic isotope effect has been observed with kH/kD equal to 0.7-0.9 and 5-7 for methyl o-acetylbenzoate and normal methyl 8-acetyl-1-naphthoate, respectively.The effect of substituents and ring-chain tautomerism on the rates has been considered.For the o-acylbenzoates the initial state is the ring-chain tautomerism equilibrium mixture and the rate-determining step is the intramolecular attack of the anion of the normal ester.For normal 8-acyl-1-naphthoates the rate-determining step is the ionisation of the normal esters; for the corresponding pseudo esters, the rate-determining step is the isomerisation of the pseudo to the normal ester.
