158471-23-9

Upstream product

• 934-56-5 trimethyl(phenyl)stannane 
• 13707-47-6 2-furaldehyde tosylimine 
• 110-00-9 furan 
• 109-72-8 n-butyllithium 
• 51608-60-7 N-(benzylidene)-p-methylbenzenesulfonamide 
• 135822-87-6 (E)-N-(furan-2-ylmethylene)-4-methylbenzenesulfonamide 
• 98-80-6 phenylboronic acid 
• 83948-38-3 C-[2]furyl-C-phenyl-methylamine 
• 98-59-9 p-toluenesulfonyl chloride 
• 5720-07-0 4-methoxyphenylboronic acid 
• 70-55-3 toluene-4-sulfonamide 
• 3262-89-3 triphenylboroxine 
• 98-01-1 furfural 
• 53387-67-0 C₁₁H₁₁NO*ClH 

Downstream Products

• 1401078-63-4 C₃₀H₂₇NO₅S 
• 1380338-00-0 C₃₀H₂₇NO₅S 
• 1213779-03-3 (2S)-1-(4-methylphenylsulfonyl)-2-phenyl-1,6-dihydro-3-(2H)-pyridinone 
• 1213779-04-4 (2S)-1-(4-Methylphenylsulfonyl)-2-phenylpiperidin-3-one 
• 1620023-58-6 C₁₈H₁₇NO₄S 
• 235787-78-7 6-phenyl-1-(4-tolylsulfonyl)-1,6-dihydropyridine-2,5-dione 
• 235787-75-4 6-hydroxy-2-phenyl-1-(4-tolylsulfonyl)-1,6-dihydro-2H-pyridin-3-one 

Relevant academic research and scientific papers

Rhodium-catalyzed and sonication-accelerated addition of aryltin and aryllead reagents to imines in air and water

In the presence of a rhodium catalyst, imines (1a-k) react with phenyltrimethyltin 2a or phenyltrimethyllead 2b in water and air under ultrasonic irradiation at 35°C to give the corresponding diarylmethylamines (3a-k) in good yields.

Rhodium-catalyzed addition of aryldifluoromethylsilanes to N-sulfonylaldimines

The addition of aryldifluoromethylsilanes to N-sulfonylaldimines was found to be catalyzed by a rhodium complex, [Rh(cod)(MeCN)2]BF4, in the presence of potassium fluoride to give the corresponding arylated N-sulfonylamines in good yield. The reaction mechanism would involve the generation of a fluoride-coordinated arylsilicate and the transmetalation between the arylsilicate and the rhodium complex to give the arylrhodium species as a key intermediate.

Enantioselective synthesis of arylglycine derivatives by Asymmetric Addition of arylboronic acids to imines

Rhodium-catalyzed enantioselective 1,2-additions of arylboronic acids to N-tosyl furanylimine and lithium 5-methyl-2-furanyltriolborate to N-tosyl arylimines giving aryl(2-furanyl)methanamines were developed for enantioselective synthesis of arylglycines

Enantioselective Rh-catalyzed arylation of N-tosylarylimines with arylboronic acids

The asymmetric arylation of N-tosylarylimines with arylboronic acids was realized by using rhodium/(S)-ShiP as catalyst. The reaction proceeded in aqueous toluene to give diarylmethylamines in good yields with up to 96% ee.

Heterogeneous Chiral Diene-Rh Complexes for Asymmetric Arylation of α,β-Unsaturated Carbonyl Compounds, Nitroalkenes, and Imines

A chiral diene ligand with tertiary alkyl amine-derived secondary amide moiety was immobilized on cross-linked polystyrene (PS) by radical polymerization, which was combined with Rh to form heterogeneous chiral Rh complexes (PS-diene Rh?Cl). PS-diene Rh?Cl catalyzed asymmetric arylation reactions of α,β-unsaturated carbonyl compounds (ketones, esters, and amides), nitroalkenes, and imines afforded the desired products in high yields with excellent enantioselectivities. PS-diene Rh?Cl is stable in air, can be stored for several months, and can be reused more than 10 times without any reduction of either yield or enantioselectivity. We also developed a method of activation of PS-diene Rh?Cl to generate more active species. (Figure presented.).

Planar-chiral phosphine-olefin ligands exploiting a (Cyclopentadienyl)manganese(I) scaffold to achieve high robustness and high enantioselectivity

A series of 2-methyl-1,3-propenylene-bridged (η5-diarylphosphinocyclopentadienyl)(phosphine)manganese(I) di-carbonyl complexes 2 have been developed as a new class of phosphine-olefin ligands based on a planar-chiral transition-metal scaffold,

Asymmetric Arylation of Imines Catalyzed by Heterogeneous Chiral Rhodium Nanoparticles

Asymmetric arylation of aldimines catalyzed by heterogeneous chiral rhodium nanoparticles has been developed. The reaction proceeded in aqueous media without significant decomposition of the imines by hydrolysis to afford chiral (diarylmethyl)amines in high yields with outstanding enantioselectivities. This catalyst system exhibited the highest turnover number (700) in heterogeneous catalysts reported to date for these reactions. The reusability of the catalyst was also demonstrated.

Development of new P-chiral P,π-dihydrobenzooxaphosphole hybrid ligands for asymmetric catalysis

A new family of P-chiral P,π-hybrid ligands was prepared from the dihydrobenzooxaphosphole core. These new ligands were demonstrated to be both sterically and electronically tunable at the substituents on the phosphorus atom and the π-system of the ligand. Application of these new ligands to the catalytic asymmetric addition of boronic acids to imine electrophiles was shown to proceed with high levels of enantioinduction. (Chemical Equation Presented).

Biomass derived furfural-based facile synthesis of protected (2S)-phenyl-3-piperidone, a common intermediate for many drugs

An efficient synthetic route towards tosyl-protected (2S)-phenyl-3- piperidone, a common intermediate for many drugs, has been developed in 5 steps in 54% yield from biomass derived furfural. The synthetic utility of the piperidone core structure was demonstrated with the synthesis of a NK 1 receptor antagonist. This journal is the Partner Organisations 2014.

3-PIPERIDONE COMPOUNDS AND THEIR USE AS NEUROKININ-1 (NK1) RECEPTOR ANTAGONISTS

The invention relates to 3-piperidone compounds, and in particular, to (2S)-phenyl-3-piperidone and its synthesis method. Use of the thus-synthesized 3-piperidone compounds as potent neurokinin-1 (NK1) receptor antagonists is also provided.