174708-24-8

Upstream product

• 108-55-4 glutaric anhydride, 
• 102312-78-7 (E)-methyl 5-phenylhex-5-enoate 
• 825-54-7 cyclopent-1-en-1-ylbenzene 
• 1501-04-8 Methyl 4-benzoylbutanoate 
• 1501-05-9 5-oxo-5-phenylvaleric acid 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 71-43-2 benzene 
• 1779-49-3 Methyltriphenylphosphonium bromide 

Downstream Products

• 174707-82-5 Se-Phenyl 5-phenylhex-5-eneselenoate 
• 20795-53-3 3-phenylcyclohexanone 
• 1258203-92-7 6-exo-6-(iodomethyl)-6-phenyltetrahydro-2H-pyran-2-one 
• 1370729-62-6 (R)-6-(iodomethyl)-6-phenyltetrahydro-2H-pyran-2-one 
• 1261280-18-5 (S)-6-(bromomethyl)-6-phenyltetrahydro-2H-pyran-2-one 
• 1261280-19-6 (R)-6-(bromomethyl)-6-phenyltetrahydro-2H-pyran-2-one 
• 127047-12-5 5-phenyl-hex-5-en-1-ol 
• 1338575-97-5 4-nitro-N-((6-oxo-2-phenyltetrahydro-2H-pyran-2-yl)methyl)benzenesulfonamide 
• 1338576-00-3 4-nitro-N-((2-phenyltetrahydro-2H-pyran-2-yl)methyl)benzenesulfonamide 
• 1338575-91-9 tert-butyl 5-phenylhex-5-enoate 
• 1392140-33-8 C₁₂H₁₃ClO₂ 
• 1537898-07-9 6-phenyl-6-(2,2,2-trifluoroethyl)tetrahydro-2H-pyran-2-one 

Relevant academic research and scientific papers

Nitroxyl Catalysts for Six-Membered Ring Bromolactonization and Intermolecular Bromoesterification of Alkenes with Carboxylic Acids

We developed a nitroxyl-catalyzed bromoesterification of alkenes with bromo reagents, which includes a six-membered ring bromolactonization of alkenyl carboxylic acids catalyzed by AZADO as the nitroxyl radical catalyst, and an intermolecular bromoesterification of alkenes with carboxylic acids using NMO as the N-oxide catalyst. We also accomplished a remote diastereoselective bromohydroxylation via an AZADO-catalyzed six-membered ring bromolactonization and a subsequent ring cleavage reaction with alkylamines to furnish ?-bromo-δ-hydroxy amides with high diastereoselectivity.

Synthesis of Novel C 2-Symmetric Sulfur-Based Catalysts: Asymmetric Formation of Halo- and Seleno-Functionalized Normal- and Medium-Sized Rings

The synthesis of novel, highly functionalized, C 2 -symmetric sulfur-based catalysts is developed and their catalytic applications are explored in asymmetric bromo-, iodo- and seleno-functionalizations of alkenoic acids. This protocol provides

Double Functionalization of Styrenes by Cu-Mediated Assisted Tandem Catalysis

The double functionalization of styrenes through Cu-mediated assisted tandem catalysis was developed. The reaction was initiated by Cu-catalyzed aziridination and the subsequent nucleophilic ring-opening, which was triggered by the addition of (NH4)2S2O8 as an oxidant of Cu-catalyst to form a variety of C–C and C–X bonds. The expansion to three contiguous catalytic cycles led to the synthesis of functionalized indolines by one-pot operation.

Synthesis of Chiral Sulfonyl Lactones via Copper-Catalyzed Asymmetric Radical Reaction of DABCO?(SO2)

In the present work, an asymmetric copper-catalyzed radical multi-component cascade reaction of an unsaturated carboxylic acid, aryldiazonium tetrafluoroborate, and DABCO?(SO2)2 (DABSO) has been developed for the enantioselective synthesis of sulfonyl lactones. In this reaction, this SO2 surrogate, DABSO was applied for the first time in the construction of chiral compounds. This multiple-step asymmetric radical reaction was carried out under mild conditions and tolerated a wide range of substrates, resulting in the corresponding sulfonyl lactones with up to 95% chemical yields and 88% ee. The current reaction enriches the research contents of DABSO, and provides a new and efficient strategy to chiral functionalized lactones bearing quarternary stereogenic center. (Figure presented.).

Visible-Light-Catalyzed Phosphonation-Annulation: an Efficient Strategy to Synthesize β-Phosphonopyrrolidines and β-Phosphonolactones

A new type of phosphine radical precursor for C—P bond formation has been developed and successfully used in visible-light-catalyzed phosphonation-annulation of unsaturated sulfonamides and carboxylic acids. The catalytic process is simple and green acces

Gold(I)-Catalyzed Enantioselective Annulations between Allenes and Alkene-Tethered Oxime Ethers: A Straight Entry to Highly Substituted Piperidines and aza-Bridged Medium-Sized Carbocycles

Piperidine scaffolds are present in a wide range of bioactive natural products and are therefore considered as highly valuable, privileged synthetic targets. In this manuscript, we describe a gold-catalyzed annulation strategy that allows a straightforward assembly of piperidines and piperidine-containing aza-bridged products from readily available alkene-tethered oxime ethers (or esters) and N-allenamides. Importantly, we demonstrate the advantages of using oxime derivatives over imines, something pertinent to the whole area of gold catalysis, and provide relevant mechanistic experiments that shed light into the factors affecting the annulation processes. Moreover, we also describe preliminary experiments demonstrating the viability of enantioselective versions of the above reactions.

Divergent Access to (1,1) and (1,2)-Azidolactones from Alkenes using Hypervalent Iodine Reagents

A versatile synthesis of azidolactones through azidation and cyclization of carboxylic acids onto alkenes has been developed. Based on either photoredox or palladium catalysis, (1,1) and (1,2) azido lactones can be selectively synthesized. The choice of catalyst and benziodoxol(on)e reagent serving as azide source was essential to initiate either a radical or Lewis acid mediated process with divergent outcome. These transformations were carried out under mild conditions using a low catalyst loading and gave access to a large scope of azido lactones.

Photoredox-Catalyzed Cascade Difluoroalkylation and Intramolecular Cyclization for Construction of Fluorinated γ-Butyrolactones

A cascade visible-light photocatalytic difluoroalkylation and intramolecular cyclization reaction has been developed for the synthesis of difluoroalkylated oxygen heterocycles. The reaction was carried out under very mild conditions, affording fluorinated

Enantioselective Organocatalyzed Bromolactonizations: Applications in Natural Product Synthesis

Asymmetric bromolactonization reactions of δ-unsaturated carboxylic acids have been investigated in the presence of 10 chiral squaramide hydrogen-bonding organocatalysts. The best catalyst enabled the cyclization of several 5-arylhex-5-enoic acids into th

Cobalt-catalyzed oxidative cyclization of gem-disubstituted conjugated alkenols

Aryl gem-disubstituted conjugated alkenols underwent oxidative cyclization affording 2,5,5-trisubstituted tetrahydrofurans in reasonable yields and good diastereoselectivities using the reductive termination variation of the Mukaiyama aerobic oxidative reaction. Under oxidative termination, the same alkenols produced diols and ketonic by-products via the double hydration and beta-scission competing pathways. Furthermore, the differences in alkenol reactivity under the reductive and oxidative termination conditions were investigated.