5724-02-7

Upstream product

• 38379-83-8 ethyl (E)-5-(4-chlorophenyl)pent-4-enoate 
• 104-88-1 4-chlorobenzaldehyde 
• 17857-14-6 (3-carboxypropyl)(triphenyl)phosphonium bromide 
• 591-80-0 pent-4-enoic acid 
• 637-87-6 1-Chloro-4-iodobenzene 
• 58824-54-7 p-chlorophenylvinylcarbinol 
• 78-39-7 Triethyl orthoacetate 
• 1073-67-2 4-vinylbenzyl chloride 
• 124-38-9 carbon dioxide 
• 214116-80-0 1-chloro-4-(cyclopropylidenemethyl)benzene 

Downstream Products

• 5822-03-7 Bis-<4-(4-chlor-benzyliden)-butyryl>-peroxid 
• 1300698-99-0 (5R,6S)-5-bromo-6-(4-chlorophenyl)tetrahydro-2H-pyran-2-one 
• 117324-73-9 (E)-5-(p-chlorophenyl)pent-4-en-1-ol 
• 15542-34-4 5-(4-chlorophenyl)penta-(2E,4E)-dienoic acid 
• 161725-12-8 5-(4-chlorophenyl)pentanoic acid 
• 1415637-25-0 C₁₁H₁₀ClIO₂ 

Relevant academic research and scientific papers

Synthesis of Antitricyclic Morpholine Derivatives through Iodine(III)-Mediated Intramolecular Umpolung Cycloaddition of Olefins

A (diacetoxyiodo)benzene-mediated intramolecular cycloaddition of olefins to construct tricyclic morpholines is presented. A series of substituted tricyclic morpholines were obtained in one-step simple operation under mild conditions, and the NMR studies

Novel highly potent OXE receptor antagonists with prolonged plasma lifetimes that are converted to active metabolites in vivo in monkeys

Background and Purpose: The 5-lipoxygenase product 5-oxo-6E,8Z,11Z,14Z-eicosatetraenoic acid (5-oxo-ETE), acting through the OXE receptor, is a potent eosinophil chemoattractant that may be an important proinflammatory mediator in eosinophilic diseases su

Enantioselective Organocatalytic Enamine C?H Oxidation/Diels- Alder Reaction

α,β-unsaturated aldehydes have been traditionally used in LUMO lowering asymmetric aminocatalysis (iminium catalysis), while the use of saturated aldehydes as substrates in this type of catalysis has been elusive, until recently. Herein, we demonstrate that organic, single-electron oxidants in the presence of diarylprolinol silylether type catalysts serve as effective tools for the transformation of electron rich enamines to iminium ions which partake in a subsequent Diels-Alder reaction. This enantioselective one-pot transformation represents the first example of saturated aldehydes being used in domino Diels-Alder reaction processes and demonstrates the power of this protocol for construction of stereo-defined chiral compounds and building blocks. (Figure presented.).

Rapid Access to Thiolactone Derivatives through Radical-Mediated Acyl Thiol-Ene and Acyl Thiol-Yne Cyclization

A new synthetic approach to thiolactones that employs an efficient acyl thiol-ene (ATE) or acyl thiol-yne (ATY) cyclization to convert unsaturated thiocarboxylic acid derivatives into thiolactones under very mild conditions is described. The high overall yields, fast kinetics, high diastereoselectivity, excellent regiocontrol, and broad substrate scope of these reaction processes render this a very useful approach for diversity-oriented synthesis and drug discovery efforts. A detailed computational rationale is provided for the observed regiocontrol.

Iridium-Catalyzed Aerobic α,β-Dehydrogenation of γ,δ-Unsaturated Amides and Acids: Activation of Both α- And β-C-H bonds through an Allyl-Iridium Intermediate

Direct aerobic α,β-dehydrogenation of γ, δ-unsaturated amides and acids using a simple iridium/copper relay catalysis system is described. We developed a new strategy that overcomes the challenging issue associated with the low α-acidity of amides and acids. Instead of α-C-H metalation, this reaction proceeds by β-C-H activation, which results in enhanced α-acidity. Conjugated dienamides and dienoic acids were synthesized in excellent yield with this reaction, which uses a simple reaction protocol. Mechanistic experiments suggest a catalyst resting state mechanism in which both α-C-H and β-C-H cleavage is accelerated.

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.

Preparation of α-Acyloxy Ketones via Visible-Light-Driven Aerobic Oxo-Acyloxylation of Olefins with Carboxylic Acids

We developed a visible-light driven oxo-acyloxylation of aryl alkenes with carboxylic acids and molecular oxygen. A metal-free photoredox system, consisting of an acridinium photocatalyst, an organic base, and molecular sieve (MS) 4 ?, promotes chemoselective aerobic photooxidation of aryl alkenes. This approach may provide a green, practical, and metal-free protocol for a wide range of α-acyloxy ketones.

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.