90819-98-0

Upstream product

• 120-74-1 endo-norbornenecarboxylic acid 
• 100-51-6 benzyl alcohol 
• 120-74-1 5-carboxybicyclo<2.2.1>hept-2-ene 
• 15082-42-5 lithium benzyloxide 
• 221482-81-1 (1'S,2'S,4'S)-(2-bicyclo<2.2.1>hept-5'-ene-2'-carbonyl)-3-phenyl-l-menthopyrazole 
• 331283-87-5 (4R,5S)-4-cyclohexyl-1,5-dimethyl-3-[(1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-ylcarbonyl]-2-imidazolidinone 
• 139109-24-3 (4R,5S)-1,5-dimethyl-3-[(1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-ylcarbonyl]-4-phenyl-2-imidazolidinone 
• 120-74-1 (1S,2S,4S)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid 
• 109-72-8 n-butyllithium 
• 542-92-7 cyclopenta-1,3-diene 
• 90719-36-1 (4R,5S)-3-((3'S,4'S,6'S)-bicyclo<2.2.1>heptene-4'-carbonyl)-4-methyl-5-phenyl-2-oxazolidinone 
• 100-39-0 benzyl bromide 
• 2495-35-4 benzylacrylate 

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 
• 634893-89-3 di-tert-butyl (7S)-7β-benzyloxycarbonyl-(1α,2β,5β,6α)-tricyclo[4.2.1.0^2,5]nona-3-ene-3,4-dicarboxylate 
• 634893-99-5 di-tert-butyl (4S,11S)-4β-(benzyloxycarbonylmethylcarbamoyl)-11β-(1-methoxycarbonylethylcarbamoyl)-16-oxa-(1α,2β,3α,6α,7β,8α,9β,10α,13α,14β)-hexacyclo[6.6.1.1^4,6.1^10,13.0^2,7.0^9,14]heptadeca-1,8-dicarboxylate 

Relevant academic research and scientific papers

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.

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.

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.

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

Strategies and methods for the attachment of amino acids and peptides to chiral [n]polynorbornane templates.

A versatile synthesis of amino acid and peptide functionalised [n]polynorbornane scaffolds is described. The frameworks are constructed using the stereoselective and regioselective cycloaddition of suitably functionalised chiral cyclobutene epoxides with similar norbornenes. The strategies employed allow a range of topologies to be accessed and a number of regioselectively addressable linkage points to be accommodated.

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.

N-Alkenoylimidazolidin-2-ones as chiral dienophiles in Diels-Alder cycloaddition reactions

Homochiral N-enoylimidazolidin-2-ones 5-8 are readily accessible, practical, and highly diastereoselective dienophiles in dialkylaluminium-promoted Diels-Alder reactions. Acrylate, methacrylate, and (E)-crotonate derivatives bearing ephedrine-based imidaz

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.

Diastereoselective Diels-Alder reaction of 2-(α,β-unsaturated)acyl-3- phenyl-1-menthopyrazoles

The reaction of 2-(α,β-unsaturated)acyl-3-phenyl-1-menthopyrazoles (9) with dienes gave Diels-Alder adducts in good yield. The addition of MgBr2 · OEt2 or ZnCl2 accelerated these reactions through the formation of chelating bonds such as N ··· Mg ··· O=C or N ··· Zn ··· O=C. The structural fixation by these catalysts also promoted the endo and diastereoselectivities of the Diels-Alder addition on the Re-face of the dienophiles. These results were supported by PM3 calculations, in which the heats of formation of the transition states anticipated the remarkable differences between the Re- and Si-facial attacks of the dienes.

Highly Regio- and Stereo-specific Preparation of a New Carbohydrate-based 1,3-Oxazin-2-one by the INIR Method and its Applications in Some Asymmetric Transformations

Preliminary experiments show that a new gulonic acid-derived 1,3-oxazin-2-one, prepared by an intramolecular nitrene insertion reaction (INIR) method, serves to control both asymmetric aldol and Diels-Alder reactions with excellent stereo-selection.