16837-94-8Relevant articles and documents
New macrolides and some sesquiterpenoid derivatives occurring in Galbanum absolute
Kaiser,Lamparsky
, p. 2671 - 2680 (1978)
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Hemperly et al.
, p. 3315,3316-3319 (1975)
A Convenient Ruthenium-Catalysed α-Methylation of Carbonyl Compounds using Methanol
Dang, Tuan Thanh,Seayad, Abdul Majeed
supporting information, p. 3373 - 3380 (2016/11/13)
An efficient ruthenium catalyst is reported, for the first time, to catalyse the α-methylation of ketones and esters using methanol as a green methylating agent. The in situ generated catalyst from the complexes [RuCp*Cl2]2or [RuCp*Cl2]nwith dpePhos provided up to quantitative yields in the presence of only 20 mol% of lithium tert-butoxide (LiO-t-Bu) as a base. Regioselective mono- or multi-methylation could be effectively controlled by temperature. This catalyst system was also effective for the one-pot sequential α-alkylation–α-methylation of methyl ketones and conjugate reduction–α-methylation of α,β-unsaturated ketones to synthesise α-branched ketones. An application of the α-methylation of esters using the ruthenium catalyst was demonstrated for an alternative catalytic synthesis of Ketoprofen. (Figure presented.).
Enzyme-mediated enantioface-differentiating hydrolysis of α-substituted cycloalkanone enol esters
Matsumoto, Kazutsugu,Tsutsumi, Seiji,Ihori, Tamiko,Ohta, Hiromichi
, p. 9614 - 9619 (2007/10/02)
A new type of enzymatic hydrolysis, enantioface-differentiating hydrolysis of enol esters, is disclosed. As a result of screening, Pichia miso IAM 4682, a type of yeast, was selected as the best strain to perform the enantioselective hydrolysis of enol esters to give α-chiral ketones. For example, incubation of 1-acetoxy-2-methylcyclohexene (4a) with P. miso afforded (S)-2-methylcyclohexanone (5) in high optical yield. This enzymatic hydrolysis is applicable to various α-substituted cycloalkanone enol esters, and thereby chiral six-, eight-, ten-, and twelve-membered-ring ketones of 70-96% enantiomeric excess (ee) are easily prepared.