158430-34-3Relevant academic research and scientific papers
A mild and efficient catalytic alkylative monofunctionalization of cyclic anhydrides
Bercot, Eric A.,Rovis, Tomislav
, p. 174 - 175 (2002)
Substituted succinic and glutaric anhydrides undergo a nickel-catalyzed monofunctionalization with organozinc reagents as nucleophiles. The reaction proceeds readily with a variety of substrates, employs commercially available or readily attainable reagents, tolerates sensitive functionality on both partners, and affords the product ketoacids in moderate to high yields. The use of a chiral phosphinooxazoline results in a desymmetrization of a meso anhydride to provide the ketoacid in 85% yield and 79% ee. Copyright
Trans-4-acetylcyclohexanecarboxylic acid and (±)-trans-2-acetylcyclohexanecarboxylic acid: Hydrogen-bonding patterns in two isomeric keto acids
Newman, Jacob M.,Thompson, Hugh W.,Lalancette, Roger A.
, (2002)
Both title compounds, C9H14O3, display carboxyl-dimer hydrogen-bonding patterns. The 4-acetyl isomer adopts a chiral conformation with negligible disordering of the methyl and carboxyl groups and forms centrosymmetric dime
Highly efficient nickel-catalyzed cross-coupling of succinic and glutaric anhydrides with organozinc reagents
Bercot, Eric A.,Rovis, Tomislav
, p. 247 - 254 (2007/10/03)
A nickel-catalyzed alkylation of succinic and glutaric anhydrides with alkyl- and arylzinc reagents has been developed. A dramatic olefin effect has been investigated resulting in the identification of several styrene-based promoters which show pronounced enhancements in reaction rate. The substrate scope with respect to electrophilic and nucleophilic coupling partners has been examined and found to be remarkably broad, allowing for rapid introduction of molecular complexity through the use of functionalized coupling partners. Regioselective alkylation of an unsymmetrical succinic anhydride and a profound effect of pendent coordinating olefins on reaction rate suggest a mechanism involving discrete oxidative addition of the nickel complex into the cyclic anhydride followed by a transmetalation event.
