193531-42-9

Upstream product

• 1712-71-6 3-chloro-α-methylstyrene 
• 99-02-5 3'-Chloroacetophenone 

Downstream Products

• 910819-14-6 3-(3-chlorophenyl)but-3-en-1-ol 

Relevant academic research and scientific papers

Chelation versus Non-Chelation Control in the Stereoselective Alkenyl sp2 C?H Bond Functionalization Reaction

A hydroxy group chelation-assisted stereospecific oxidative cross-coupling reaction between alkenes was developed under mild reaction conditions. In the presence of palladium catalyst, the alkenes tethered with hydroxy functionality can couple efficiently with electron-deficient alkenes to form the corresponding multi-substituted olefin products. The hydroxy group on the substrate could play dual roles in reaction, acting as the directing group for alkenyl C?H bond activation and controlling the stereoselectivity of the products.

The cascade coupling/iodoaminocyclization reaction of trifluoroacetimidoyl chlorides and allylamines: metal-free access to 2-trifluoromethyl-imidazolines

A metal-free cascade coupling/iodoaminocyclization reaction for the rapid assembly of 2-trifluoromethyl-imidazolines has been disclosed. The transformation applies readily accessible trifluoroacetimidoyl chlorides, allylamines andN-iodosuccinimides as the starting substrates, achieving an efficient and straightforward pathway to construct diverse imidazoline derivatives. Excellent efficiency of the reaction is observed (higher than 90% isolated yield for half of the examples), and the obtained imidazoline products bearing a pendent iodomethyl group could be easily transformed into other synthetically valuable compounds.

Visible-light-promoted radical alkylation/cyclization of allylic amide with N-hydroxyphthalimide ester: Synthesis of oxazolines

An efficient photocatalytic alkylation/cyclization of allylic amide with N-hydroxyphthalimide ester has been developed. The transformation is taken advantage of alkyl radicals to attack allylic amide with the assist of inexpensive rose bengal as photocatalyst to prepare a series of alkyl substituted oxazolines in moderate to excellent yields. High regioselectivity, operational safety, mild conditions and excellent substrate generality give this protocol broad application prospects.

HETEROAROMATIC COMPOUNDS AS VANIN INHIBITORS

The present invention encompasses compounds of the formula I which are suitable for the treatment of diseases related to Vanin, and processes for making these compounds, pharmaceutical preparations containing these compounds, and their methods of use.

Chiral Br?nsted Acid Catalyzed Dynamic Kinetic Asymmetric Hydroamination of Racemic Allenes and Asymmetric Hydroamination of Dienes

The first highly efficient and practical chiral Br?nsted acid catalyzed dynamic kinetic asymmetric hydroamination (DyKAH) of racemic allenes and asymmetric hydroamination of unactivated dienes with both high E/Z selectivity and enantioselectivity are described herein. The transformation proceeds through a new catalytic asymmetric model involving a highly reactive π-allylic carbocationic intermediate, generated from racemic allenes or dienes through a proton transfer mediated by an activating/directing thiourea group. This method affords expedient access to structurally diverse enantioenriched, potentially bioactive alkenyl-containing aza-heterocycles and bicyclic aza-heterocycles.

Highly Enantioselective Iridium-Catalyzed Hydrogenation of 2-Aryl Allyl Phthalimides

The iridium-catalyzed asymmetric hydrogenation of 2-aryl allyl phthalimides to afford enantioenriched β-aryl-β-methyl amines is presented. Recently developed Ir-MaxPHOX catalysts are used for this enantioselective transformation. The mild reaction conditions and the feasible removal of the phthalimido group makes this catalytic method easily scalable and of great interest to afford chiral amines. The importance of this new methodology is exemplified by the formal synthesis of (R)-Lorcaserin, OTS514, and enantiomerically enriched 3-methyl indolines.

A Copper Catalyst with a Cinchona-Alkaloid-Based Sulfonamide Ligand for Asymmetric Radical Oxytrifluoromethylation of Alkenyl Oximes

A copper-catalyzed asymmetric radical oxytrifluoromethylation of alkenyl oxime and Togni's reagent has been successfully developed, thereby providing straightforward access to CF3-containing isoxazolines bearing α-tertiary stereocenters with excellent yield and enantioselectivity. The key to success is the rational design of cinchona-alkaloid-based sulfonamides as neutral/anionic hybrid ligands to effectively control the stereochemistry in copper-catalyzed reactions involving free alkyl radical species. The utility of this method is illustrated by efficient transformation of the products into useful chiral CF3-containing 1,3-aminoalcohols.

Copper-catalyzed radical oxytrifluoromethylation of alkenyl oximes at ambient temperature

A mild and efficient copper-catalyzed radical oxytrifluoromethylation reaction of alkenyl oximes was successfully developed. The method provides a straightforward access to a wide range of CF3-containing isoxazolines in good to excellent yields.

Visible-Light Photocatalytic Bicyclization of 1,7-Enynes toward Functionalized Sulfone-Containing Benzo[a]fluoren-5-ones

A new visible-light photocatalytic arylsulfonylation and bicyclization of C(sp3)-tethered 1,7-enynes with sulfinic acids has been developed, delivering functionalized sulfone-containing benzo[a]fluoren-5-ones with generally good yields. This Eosin Y-catalyzed approach makes use of visible light as a safe and eco-friendly energy source to drive cascade cyclization reactions, resulting in continuous multiple bond-forming events including C–S and C–C bonds to efficiently construct polycyclic-linked alkyl aryl sulfones. (Figure presented.).

Catalytic enantioselective iodoetherification of oximes

Organocatalysis: The first catalytic enantioselective iodoetherification of oximes is developed using commercially available N-iodosuccinimide. In the presence of a dihydrocinchonidine-derived thiourea (10 mol %), β,γ-unsaturated oximes undergo facile iodoetherification to produce Δ2-isoxazolines containing a quaternary stereogenic center generally in high yield with good to excellent enantioselectivity. Copyright