72175-11-2Relevant academic research and scientific papers
Synthesis of γ-lactones and unsaturated bis γ-lactones via Cu-Fe-mediated reductive cyclization of di- and tri-α-halogenated carboxylic esters
Somech, Iris,Shvo, Youval
, p. 153 - 159 (2000)
A new synthetic route to γ-substituted γ-butyrolactones from alkenes and α-dichloro ester, in the presence of CuCl (catalytic) and Fe(0) (stoichiometric) in acetonitrile, was established. A study of this reaction has demonstrated that the overall process consists of the following reaction steps: (a) addition of the dichloro ester to the olefin via CuCl catalysis; (b) selective reduction of the α-chloro atom in the resulting adduct by Fe(0); (c) cyclization of the resulting γ-chloro ester to γ-butyrolactone. Yields were improved by first carrying out step (a), then steps (b) and (c) in one pot. Selectivity was improved in the presence of a small amount of water. α-Trichloro esters also generated the γ-substituted γ-butyrolactone, albeit in lower yields and selectivity. The latter reaction gave rise to the formation of interesting by-products, namely new unsaturated bis-lactones.
Merging domino and redox chemistry: Stereoselective access to di- and trisubstituted β,γ-unsaturated acids and esters
Tejedor, David,Mendez-Abt, Gabriela,Cotos, Leandro,Garcia-Tellado, Fernando
supporting information; experimental part, p. 3468 - 3472 (2012/04/23)
Merging is the game! The coupling of a domino reaction and an internal neutral redox reaction constitutes an excellent manifold for the stereoselective synthesis of di- and trisubstituted olefins featuring a malonate unit, an ester, or a free carboxylic acid as substituents at the allylic position (see scheme; MW=microwave). The reaction utilizes simple starting materials (propargyl vinyl ethers), methanol or water as solvents, and a very simple and bench-friendly protocol. Copyright
A versatile and convenient protocol for the stereocontrolled synthesis of olefinic insect pheromones
Vasil'ev, Andrei A.,Vlasyuk, Alexei L.,Gamalevich, Galina D.,Serebryakov, Edward P.
, p. 389 - 400 (2007/10/03)
A combination of the Horner-Emmons synthesis of alkyl 2,4-dienoates with their hydrogenation over complex L·Cr(CO)3 catalysts (L = 3CO or arene) provides a versatile, stereocontrolled and operationally simple approach to the (Z)-disubstituted, (Z)-trisubstituted, (E)-trisubstituted alkenes and skipped (Z,Z)-disubstituted diolefins with a homoallylic type of function. This protocol, sometimes supplemented by an enzymatic hydrolysis, was successfully applied to the synthesis of configurationally pure (gp ≥ 98%) pheromones of the furniture carpet beetle, dry bean beetle, rusty grain beetle, square-necked grain beetle and of a trail-following pheromone mimic for subterranean termites
