4926-12-9

Upstream product

• 52927-40-9 dimethyl 2-(4-fluorobenzylidene)malonate 
• 459-32-5 4-fluorocinnamic acid 
• 223513-93-7 diethyl 3-(4-fluorophenyl)pentanedioate 
• 459-57-4 4-fluorobenzaldehyde 
• 3449-63-6 3-(4-fluorophenyl)pentan-1,5-dioic acid 
• 100891-10-9 methyl p-fluorocinnamate 

Downstream Products

• 4759-75-5 3-(4-fluorophenyl)-glutaric acid monomethyl ester 
• 865367-14-2 (S)-3-(4-fluorophenyl)-glutaric acid monoallyl ester 
• 865367-12-0 (S)-3-(4-fluorophenyl)-glutaric acid monobutyl ester 
• 349446-94-2 (4R,1'S)-4-(4-fluorophenyl)-1-(1'-phenylethyl)piperidin-2-one 
• 349446-96-4 {(3S,4R)-4-(p-fluorophenyl)-3-(hydroxymethyl)-1-[1-(S)-phenylethyl]}piperidine 
• 349446-92-0 (3R)-3-(4-fluorophenyl)-5-hydroxypentanoic acid (1S)-1-phenylethylamide 
• 349446-93-1 (3S)-5-bromo-3-(4-fluorophenyl)pentanoic acid (1S)-1-phenylethylamide 
• 349446-95-3 (3S,4R,1'S)-4-(4-fluorophenyl)-3-methoxycarbonyl-1-(1'-phenylethyl)piperidin-2-one 
• 349446-97-5 Methanesulfonic acid (3S,4R)-4-(4-fluoro-phenyl)-1-((S)-1-phenyl-ethyl)-piperidin-3-ylmethyl ester 
• 1220248-47-4 (S)-4-(4-fluorophenyl)-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Enantioselective Desymmetrization of Glutarimides Catalyzed by Oxazaborolidines Derived from cis-1-Amino-indan-2-ol

Enantioselective reductive desymmetrization of glutarimides has been achieved employing an oxazaborolidine catalyst derived from cis-1-amino-indan-2-ol. The reaction was found to proceed through a stereoablative process that upgraded the enantioselectivity of an intermediate hydroxy-lactam. The reaction was generally tolerant of a number of substituents in the 4-position, giving enantiomeric excesses of greater than 82%.

A family of novel bifunctional organocatalysts: Highly enantioselective alcoholysis of meso cyclic anhydrides and its application for synthesis of the key intermediate of P2X7 receptor antagonists

A family of novel squaramides/sulfamides based on 1,2-alkamine was developed as chiral bifunctional catalysts to promote the asymmetric alcoholysis of meso cyclic anhydrides. The hemiesters were obtained in high yield with up to 93% ee. The usefulness of this methodology was demonstrated in the asymmetric synthesis of the key intermediate of P2X7 receptor antagonists.

An enantiodivergent and formal synthesis of paroxetine enantiomers by asymmetric desymmetrization of 3-(4-fluorophenyl)glutaric anhydride with a chiral SuperQuat oxazolidin-2-one

The asymmetric desymmetrization of 3-(4-fluorophenyl)glutaric anhydride 9 with lithiated chiral oxazolidin-2-one 8 has been studied. The desymmetrized product was formed with >90% de and converted into known intermediates for both (+)- and (-)-paroxetines.

ALLOSTERIC PROTEIN KINASE MODULATORS

The invention provides specific small molecule compounds that allosterically regulate the activity or modulate protein-protein interactions of AGC protein kinases and the Aurora family of protein kinases, methods for their production, pharmaceutical compositions comprising same, and their use for preparing medicaments for the treatment and prevention of diseases related to abnormal activities of AGC protein kinases or of protein kinases of the Aurora family.

Pilot-plant preparation of 3,4-dihydropyridin-2-one derivatives, the core structures ofP2X7 receptor antagonists

The pilot-plant syntheses of 3 and 4, the core structures of a series of P2X7 antagonists are described. The sole stereogenic center in the dihydropyridinone ring was generated by catalytic desymmetrization. Selective formylation, followed by a tandem imination/lactamization sequence, produced the 3,4-dihydropyridin-2-one ring. The compounds 3 and 4 were produced at multikilogram scale in good overall yield (～22% over six steps) and excellent stereochemical purity (97% ee for 3, 100% ee for 4).

The first asymmetric synthesis of a 4-aryl-substituted 5-carboxy-3,4-dihydropyridin-2-one derivative

A simple and practical route for the asymmetric synthesis of (S)-4-(4-fluorophenyl)-1,4,5,6-tetrahydro-6-oxo-3-pyridinecarboxylic acid (1) is presented. The procedure comprises catalytic desymmetrization of a meso-anhydride using a chiral thiourea organocatalyst, followed by selective formylation and cyclization.

ALLOSTERIC PROTEIN KINASE MODULATORS

The invention provides specific small molecule compounds that allosterically regulate the activity or modulate protein-protein interactions of AGC protein kinases and the Aurora family of protein kinases, methods for their production, pharmaceutical compositions comprising same, and their use for preparing medicaments for the treatment and prevention of diseases related to abnormal activities of AGC protein kinases or of protein kinases of the Aurora family.

Enantioselective alcoholysis of meso-glutaric anhydrides catalyzed by Cinchona-based sulfonamide catalysts

The bifunctional Cinchona-based sulfonamide catalysts showed the highest levels of enantioselectivity reported to date in the alcoholytic desymmetrization of meioglutaric anhydrides. Density functional theory (DFT) computational studies provide detailed insight into the observed sense of enantioselectivity. Moreover, detailed experimental studies and single crystal X-ray analysis confirmed that these bifunctional organocatalysts 3 do not form Hbonded self-aggregates in both solution and solid state. The synthetic utility of this methodology was also demonstrated in the synthesis of pharmaceutically important γ-amino acids, such as (S)-pregabalin. Of the many asymmetric syntheses of enantiomerically pure (S)-pregabalin reported to date, our synthesis requires the least number of and the simplest steps.

Chemoselective hydrogenation of imides catalyzed by Cp*Ru(PN) complexes and its application to the asymmetric synthesis of paroxetine

This work represents the first catalytic hydrogenation of imides into amides and primary alcohols, in which the unique chemoselectivity is originated from the bifunctional nature of ruthenium-NH moiety in the catalyst. Copyright

Enzymatic desymmetrization of 3-arylglutaric acid anhydrides

Optically active (R)- and (S)-3-arylglutaric acid monoesters 3 were synthesized in quantitative yields and good stereoselectivities by lipase-catalyzed desymmetrization of the corresponding 3-arylglutaric anhydrides 2 with alcohols. It was observed that the stereochemical outcome of the reaction was influenced by the substituents present on the aromatic ring. The influence of the enzyme, alcohol, and solvent was systematically examined. Absolute configurations of the monoesters 3 were assigned by chemical correlation to corresponding lactones 4.