770-36-5

Upstream product

• 53045-69-5 3-chloro-2-phenyl-tetrahydro-furan 
• 75-21-8 oxirane 
• 917-64-6 methyl magnesium iodide 
• 103-64-0 bromostyrene 
• 7515-38-0 (E)-4-phenylbut-3-en-1-amine 
• 100-52-7 benzaldehyde 
• 19493-09-5 Methylenetriphenylphosphorane 
• 2243-53-0 styrylacetic acid 
• 14580-93-9 2,2,2-Triphenyl-1,2-λ⁵-oxaphospholan 
• 60-29-7 diethyl ether 
• 110-86-1 pyridine 
• 67-56-1 methanol 
• 28525-69-1 (4E)-5-phenyl-4-pentenoic acid 
• 1007-03-0 1-phenyl-1-cyclopropylmethanol 

Downstream Products

• 20473-78-3 acetic acid-(4-phenyl-but-3-enyl ester) 
• 99376-56-4 4-phenyl-3-buten-1-yl 3,3-dimethyl-2-phenylcyclopropenecarboxylate 
• 105632-42-6 4-Phenyl-3,4-epoxy-1-butanol 
• 16133-83-8 tetrahydro-2-phenylfuran 
• 1330074-82-2 C₁₉H₁₆ClNO 
• 5558-00-9 (4-bromo-1-buten-1-yl)benzene 
• 1352632-27-9 C₁₉H₁₆ClNO 
• 1352632-28-0 C₂₀H₁₈ClNO 
• 68975-07-5 3-benzyltetrahydrofuran-2-one 
• 13019-37-9 α-phenyl δ-valerolactone 
• 7515-46-0 (E)-(4-chlorobut-1-en-1-yl)benzene 
• 1025966-70-4 C₁₁H₁₁ClO₂ 
• 145576-38-1 (E)-4-phenylbut-3-en-1-yl 2-diazoacetate 
• 7515-41-5 (E)-(4-bromobut-1-en-1-yl)benzene 

Relevant academic research and scientific papers

Palladium-Catalyzed Tandem Hydrocarbonylative Lactamization and Cycloaddition Reaction for the Construction of Bridged Polycyclic Lactams

The intramolecular hydroaminocarbonylation of alkenes is a compelling tool to rapidly access lactam, a privileged motif ubiquitous in natural products, pharmaceuticals, and agrochemicals. However, selective carbonylation to bridged polycyclic lactams with a lactam nitrogen at a bridgehead position is less explored. We herein report a modular palladium-catalyzed approach to perform a tandem hydrocarbonylative lactamization/Diels-Alder cycloaddition reaction with 2-vinyl aryl aldimines, alkenes, and CO, which offers convenient access to furnish the bridged polycyclic lactams in high yields with high selectivities.

Radical C(sp3)-H Heck-type Reaction of N-Alkoxybenzimidoyl Chlorides with Styrenes to Construct Alkenols

We report the first radical C(sp3)-H Heck-type reaction of aliphatic alcohols for selective δ- and ?-alkenol synthesis by photoredox catalysis. N-Alkoxybenzimidoyl chlorides are developed as novel alkoxyl radical precursors with tunable redox potentials. Various alkenols can be constructed by the inert C(sp3)-H Heck-type reaction of 4-cyano-N-alkoxybenzimidoyl chlorides with styrene derivatives under redox-neutral conditions, which can be performed on the gram scale and can be easily derivatized.

Are bis(pyridine)iodine(i) complexes applicable for asymmetric halogenation?

Enantiopure halogenated molecules are of tremendous importance as synthetic intermediates in the construction of pharmaceuticals, fragrances, flavours, natural products, pesticides, and functional materials. Enantioselective halofunctionalizations remain

Highly Regioselective 5-endo-tet Cyclization of 3,4-Epoxy Amines into 3-Hydroxypyrrolidines Catalyzed by La(OTf)3

Highly regioselective intramolecular aminolysis of 3,4-epoxy amines has been achieved. Key features of this reaction are (1) chemoselective activation of epoxides in the presence of unprotected aliphatic amines in the same molecules by a La(OTf)3 catalyst and (2) excellent regioselectivity for anti-Baldwin 5-endo-tet cyclization. This reaction affords 3-hydroxy-2-alkylpyrrolidines stereospecifically in high yields. DFT calculations revealed that the regioselectivity might be attributed to distortion energies of epoxy amine substrates. The use of this reaction was demonstrated by the first enantioselective synthesis of an antispasmodic agent prifinium bromide.

Directed Nickel-Catalyzed Diastereoselective Reductive Difunctionalization of Alkenyl Amines

We report herein an intermolecular syn-arylalkylation and alkenylalkylation of alkenyl amines with two different organohalides (iodides and bromides) using Ni(II) catalyst. The cleavable bidentate quinolinamide is utilized after extensive directing group screening to enable olefin difunctionalization with high levels of regio-, chemo-, and diastereocontrol. This general and practical protocol is compatible with α- or β-substituted terminal alkenes and internal alkenes, providing rapid access to branched aliphatic amines bearing two skipped and vicinal stereocenters with high diastereoselectivities that would otherwise be difficult to synthesize.

Intramolecular N-Me and N-H aminoetherification for the synthesis ofN-unprotected 3-amino-O-heterocycles

A mild Rh-catalyzed method for synthesis of cyclic unprotected N-Me and N-H 2,3-aminoethers using an olefin aziridination-aziridine ring-opening domino reaction has been developed. The method is readily applicable to the stereocontrolled synthesis of a va

Nickel-Catalyzed 1,2-Carboamination of Alkenyl Alcohols

An alcohol-directed, nickel-catalyzed three-component umpolung carboamination of unactivated alkenes with aryl/alkenylboronic esters and electrophilic aminating reagents is reported. This transformation is enabled by specifically tailored O-(2,6-dimethoxybenzoyl)hydroxylamine electrophiles that suppress competitive processes, including undesired β-hydride elimination and transesterification between the alcohol substrate and electrophile. The reaction delivers the desired 1,2-carboaminated products with generally high regio- and syn-diastereoselectivity and exhibits a broad scope of coupling partners and alkenes, including complex natural products. Various mechanistic experiments and analysis of the stereochemical outcome with a cyclic alkene substrate, as confirmed by X-ray crystallographic analysis, support alcohol-directed syn-insertion of an organonickel(I) species.

Nickel-Catalyzed Hydroarylation of in Situ Generated 1,3-Dienes with Arylboronic Acids Using a Secondary Homoallyl Carbonate as a Surrogate for the 1,3-Diene and Hydride Source

The nickel-catalyzed hydroarylation of 1,3-dienes with arylboronic acids using a secondary homoallyl carbonate as a surrogate for the 1,3-diene and hydride source has been developed. The synthetic strategy allowed an efficient access to a wide array of hydroarylation products in high yields with high functional group compatibility without the use of an external hydride source. Mechanistic experiments indicated that the alkene-directed oxidative addition and subsequent β-hydride elimination would be a critical process in this transformation.

An Enzymatic Platform for the Highly Enantioselective and Stereodivergent Construction of Cyclopropyl-δ-lactones

Abiological enzymes offers new opportunities for sustainable chemistry. Herein, we report the development of biological catalysts derived from sperm whale myoglobin that exploit a carbene transfer mechanism for the asymmetric synthesis of cyclopropane-fused-δ-lactones, which are key structural motifs found in many biologically active natural products. While hemin, wild-type myoglobin, and other hemoproteins are unable to catalyze this reaction, the myoglobin scaffold could be remodeled by protein engineering to permit the intramolecular cyclopropanation of a broad spectrum of homoallylic diazoacetate substrates in high yields and with up to 99 % enantiomeric excess. Via an alternate evolutionary trajectory, a stereodivergent biocatalyst was also obtained for affording mirror-image forms of the desired bicyclic products. In combination with whole-cell transformations, the myoglobin-based biocatalyst was used for the asymmetric construction of a cyclopropyl-δ-lactone scaffold at a gram scale, which could be further elaborated to furnish a variety of enantiopure trisubstituted cyclopropanes.

Direct Synthesis of Enones by Visible-Light-Promoted Oxygenation of Trisubstituted Olefins Using Molecular Oxygen

A one-step synthesis of enones from olefins is described. The reaction was performed under visible-light irradiation in the presence of molecular oxygen and a photocatalyst. The reaction proceeded with various types of trisubstituted olefins to give enones in good yields with high regioselectivity. In particular, oxygen- and nitrogen-containing functional groups, heteroaromatic rings, and cyclopropanes were tolerated. Mechanistic studies and previous reports indicated that the active oxygen species generated in the reaction system is singlet oxygen.