19039-94-2Relevant articles and documents
3-(3,4,5-Trimethoxyphenyl)-1-oxo-2-propene: A novel pharmacophore displaying potent multidrug resistance reversal and selective cytotoxicity
Das, Umashankar,Kawase, Masami,Sakagami, Hiroshi,Ideo, Atsushi,Shimada, Jun,Molnar, Joseph,Barath, Zoltan,Bata, Zsuzsanna,Dimmock, Jonathan R.
, p. 3373 - 3380 (2007)
This study revealed that various alicyclic and acyclic compounds containing the 3-(3,4,5-trimethoxyphenyl)-2-propenoyl group displayed potent MDR reversal properties. In particular, a concentration of 4 μg/ml of 2,5-bis(3,4,5-trimethoxyphenylmethylene)cyc
Enolate-Based Regioselective Anti-Beckmann C-C Bond Cleavage of Ketones
Jahn, Ullrich,Ma?ek, Tomá?
, p. 11608 - 11632 (2021/09/02)
The Baeyer-Villiger or Beckmann rearrangements are established methods for the cleavage of ketone derivatives under acidic conditions, proceeding for unsymmetrical precursors selectively at the more substituted site. However, the fragmentation regioselectivity cannot be switched and fragmentation at the less-substituted terminus is so far not possible. We report here that the reaction of ketone enolates with commercial alkyl nitrites provides a direct and regioselective way of fragmenting ketones into esters and oximes or ω-hydroxyimino esters, respectively. A comprehensive study of the scope of this reaction with respect to ketone classes and alkyl nitrites is presented. Control over the site of cleavage is gained through regioselective enolate formation by various bases. Oxidation of kinetic enolates of unsymmetrical ketones leads to the otherwise unavailable "anti-Beckmann"cleavage at the less-substituted side chain, while cleavage of thermodynamic enolates of the same ketones represents an alternative to the Baeyer-Villiger oxidation or the Beckmann rearrangement under basic conditions. The method is suited for the transformation of natural products and enables access to orthogonally reactive dicarbonyl compounds.
Thermal decarboxylative Nazarov cyclization of cyclic enol carbonates involving chirality transfer
Kozuma, Akane,Komatsuki, Keiichi,Saito, Kodai,Yamada, Tohru
supporting information, p. 60 - 63 (2019/12/12)
Decarboxylative Nazarov cyclization of chiral cyclic enol carbonates proceeded to afford chiral 2-cyclopentenones with excellent chirality transfer under thermal conditions without any catalyst. Interestingly, the thermal decarboxylative Nazarov cyclization furnished the desired product with better chirality transfer than the Lewis acid-catalyzed reaction.