445477-03-2

Upstream product

• 17857-14-6 (3-carboxypropyl)(triphenyl)phosphonium bromide 
• 529-20-4 2-methylphenyl aldehyde 
• 939400-91-6 5-o-tolylpent-4-enoic acid ethyl ester 
• 881013-16-7 1-(cyclopropylidenemethyl)-2-methylbenzene 
• 124-38-9 carbon dioxide 
• 603-35-0 triphenylphosphine 

Downstream Products

• 445477-05-4 5-(2-methylphenyl)-4-pentenoic acid methyl ester 
• 1300698-91-2 (5R,6S)-5-bromo-6-o-tolyltetrahydro-2H-pyran-2-one 
• 1380523-52-3 (E)-5-o-tolylpent-4-enyl methanesulfonate 
• 105337-73-3 (E)-5-o-tolylpent-4-en-1-ol 

Relevant academic research and scientific papers

Reversing the Regioselectivity of Halofunctionalization Reactions through Cooperative Photoredox and Copper Catalysis

Halofunctionalization of alkenes is a classical method for olefin difunctionalization. It gives rise to adducts which are found in many natural products and biologically active molecules, and offers a synthetic handle for further manipulation. Classically, this reaction is performed with an electrophilic halogen source and leads to regioselective formation of the halofunctionalized adducts. Herein, we demonstrate a reversal of the native regioselectivity for alkene halofunctionalization through the use of an acridinium photooxidant in conjunction with a copper cocatalyst.

Aminothiocarbamate-catalyzed asymmetric bromolactonization of 1,2-disubstituted olefinic acids

An efficient and enantioselective bromolactonization of 1,2-disubstituted olefinic acids using an amino-thiocarbamate catalyst has been developed, resulting in the formation of δ-lactones containing two chiral centers with up to 99% yield, 95% ee.

Solvent and ligand partition reaction pathways in nickel-mediated carboxylation of methylenecyclopropanes

Methylenecyclopropanes are carboxylated with gaseous carbon dioxide in the presence of a stoichiometric amount of a nickel complex; the reaction pathways are significantly influenced by the reaction solvent and the amine ligand. The Royal Society of Chemi

Reagent-Controlled Asymmetric Iodolactonization Using Cinchona Alkaloids as Chiral Sources

A novel method for reagent-controlled asymmetric iodolactonization of 5-aryl-4-pentenoic acids is reported. This work uses carboxylate ion pairs combined with cinchona alkaloids as chiral sources of carboxylate anion for the first time leading to a mixture of two regio-isomeric iodolactones with moderate enantioselectivity (exo-18.5% ee, endo-35.0% ee) under mild reaction conditions.

5-(2-methylphenyl)-4-pentenoic acid from a terrestrial Streptomycete

From a terrestrial Streptomycete, GW 10/2517, the new 5-(2-methylphenyl)-4-pentenoic acid (1a) was isolated. The structure of 1a was proven by a detailed spectroscopic analysis and by synthesis.