90719-45-2

Upstream product

• 120-74-1 endo-norbornenecarboxylic acid 
• 100-51-6 benzyl alcohol 
• 120-74-1 5-carboxybicyclo<2.2.1>hept-2-ene 
• 90719-33-8 (4S)-3-((3'R,4'R,6'R)-bicyclo[2.2.1]heptene-4'-carbonyl)-4-(1-methylethyl)-2-oxazolidinone 
• 90719-34-9 (4S)-3-((3'R,4'R,6'R)-bicyclo[2.2.1]heptene-4'-carbonyl)-4-(phenylmethyl)-2-oxazolidinone 
• 131564-05-1 3-[(1R,2R,4R)-bicyclo[2.2.1]hept-5-ene-2-carbonyl]oxazolidin-2-one 
• 542-92-7 cyclopenta-1,3-diene 
• 2495-35-4 benzylacrylate 
• 77-73-6 bi(cyclopentadiene) 
• 15082-42-5 lithium benzyloxide 
• 100-39-0 benzyl bromide 

Downstream Products

• 145117-47-1 (1R,2R,4R,5S)-5-Acetoxy-bicyclo[2.2.1]heptane-2-carboxylic acid benzyl ester 
• 145117-46-0 (1S,2R,4R,6R)-6-Acetoxy-bicyclo[2.2.1]heptane-2-carboxylic acid benzyl ester 

Relevant academic research and scientific papers

Oxathiaborolium-Catalyzed Enantioselective [4 + 2] Cycloaddition and Its Application in Lewis Acid Coordinated and Chiral Lewis Acid Catalyzed [4 + 2] Cycloaddition

The nascency of second-generation sulfur-stabilized borenium cations by halophilic Lewis acid SnCl4 leads to highly active chiral Lewis acids that are very effective catalysts for [4 + 2] cycloaddition. Oxathiaborolium pentachlorostannate (5-10 mol %) successfully catalyzed cycloaddition of various dienes and dienophiles to afford cycloadducts with excellent enantioselectivity (20 examples, up to 99% ee). This super Lewis acid also exhibited good enantioselectivity for the first Lewis acid coordinated and chiral Lewis acid catalyzed [4 + 2] cycloaddition to α,β-unsaturated mixed ester amide.

Fragment-Based Discovery of Pyrazolopyridones as JAK1 Inhibitors with Excellent Subtype Selectivity

Herein, we report the discovery of a series of JAK1-selective kinase inhibitors with high potency and excellent JAK family subtype selectivity. A fragment screening hit 1 with a pyrazolopyridone core and a JAK1 bias was selected as the starting point for our fragment-based lead generation efforts. A two-stage strategy was chosen with the dual aims of improving potency and JAK1 selectivity: Optimization of the lipophilic ribose pocket-targeting substituent was followed by the introduction of a variety of P-loop-targeting functional groups. Combining the best moieties from both stages of the optimization afforded compound 40, which showed excellent potency and selectivity. Metabolism studies in vitro and in vivo together with an in vitro safety evaluation suggest that 40 may be a viable lead compound for the development of highly subtype-selective JAK1 inhibitors.

Oxathiaborolium: A type of chiral Lewis acid catalyst and its application in catalytic and highly enantioselective Diels-Alder reactions

The first reported sulfur-stabilized borenium cations were synthesized through halide abstraction of a haloborane intermediate by halophilic reagents. Different from the well-known cationic oxazaborolidines, a sulfide instead of an amine was used to not only simplify the preparation of the catalysts but also increase Lewis acidity of the boron atom. The in situ generated borenium salts showed exceptional Lewis acidity and successfully catalyzed asymmetric Diels-Alder reactions of cyclopentadiene and dienophiles in excellent yields and enantioselectivities. The NMR studies of these oxathiaborolium structures were reported as well.

New and facile synthesis of aminobicyclo[22.1]heptane-2-carboxylic acids

Abstract A facile approach for the stereoselective synthesis of a- and b-2-aminobicyclo[2.2.1]heptane-2-carboxylic acid is described. Substrate-controlled α-carboxylation of norbonene monoester delivered the asymmetric diester intermediate with high diastereoselectivity (up to 35:1). Sequential chemoselective ester cleavage, Curtius rearrangement, and hydrolysis gave the a- and b-isomers of 2-aminobicyclo[2.2.1]heptane-2-carboxylic acid, respectively.

Molecular imprinted polymers binding low functionality templates

A series of highly specific molecular imprinted polymers (MIPs) for small, low functionality bicyclic Diels-Alder products was prepared as bulk polymers.

Ultracentrifuge-mediated Diels-Alder reaction in a two-phase system of water and chloroform

Dramatic acceleration of the Diels-Alder reaction of acrylate ester or methacrolein with cyclopentadiene has been observed under ultracentrifugation conditions in the presence of water, when water-CHCl3 two-phase system was employed. The Diels-Alder reaction proceeds in the lower organic phase under ultracentrifugation-induced high pressure with the upper water phase acting like a weight. Copyright

Diastereoselective Diels-Alder reactions of α-fluorinated α,β-unsaturated carbonyl compounds: Chemical consequences of fluorine substitution. 2

Two α-fluoro α,β-unsaturated carbonyl compounds, i.e., benzyl 2-fluoroacrylate (3) and 2-fluorooct-1-en-3-one (4), as well as the corresponding nonfluorinated parent compounds, were synthesized and subjected to Diels-Alder reactions with cyclopentadiene. The cycloadditions were conducted thermally, microwave-assisted, and Lewis acid-mediated (TiCl4). The fluorinated dienophiles exhibited a lower reactivity and exo diastereoselectivity, while the corresponding nonfluorinated parent compounds reacted endo selectively. DFT calculations suggest that kinetic effects of fluorine determine the stereoselectivity rather than higher thermodynamic stability of the exo products.

Lewis acid catalysis in supercritical carbon dioxide. Use of scandium tris(heptadecafluorooctanesulfonate) as a Lewis acid catalyst in Diels-Alder and aza Diels-Alder reactions

Diels-Alder reactions of carbonyl dienophiles with dienes and aza Diels-Alder reactions of imines with a diene have been successfully carried out using scandium tris(heptadecafluorooctanesulfonate) (Sc(OSO2C8F17)3) as a Lewis acid catalyst in supercritical carbon dioxide (scCO2). It was revealed that the length of perfluorocarbon chains of the scandium catalyst was an essential factor for the catalytic activity in scCO2.

Asymmetric Diels-Alder reactions of 2-fluoroacrylic acid derivatives. Part 1: The construction of fluorine substituted chiral tertiary carbon

For the construction of chiral monofluorinated tertiary carbons, we have examined the asymmetric Diels-Alder reaction of 2-fluoroacrylic acid derivatives beating a chiral oxazolidinone moiety. Under diethylaluminum chloride catalyzed conditions at - 100°C

Transesterification of N-acyloxazolidinones with alcohol by lanthanum(III) iodide

Transesterification of N-acyloxazolidinones by treatment with an alcohol and lanthanum(III) iodide gives the corresponding esters in good to excellent yields under mild conditions with negligible racemization.