415902-37-3

Upstream product

• 55262-02-7 3-benzyl-cyclobutanone 
• 300-57-2 allylbenzene 
• 21175-42-8 (±)-5-benzyldihydrofuran-2(3H)-one 
• 3183-15-1 4-oxo-5-phenylvaleric acid 
• 140-29-4 phenylacetonitrile 
• 100-52-7 benzaldehyde 
• 74725-45-4 (E)-2-benzylidenecyclobutan-1-one 
• 928215-58-1 2-benzyl-2-hydroxy-1-methylpyrrrolidin-5-one 
• 100-44-7 benzyl chloride 
• 1204181-95-2 1-phenyl-pent-4-yn-2-(S)-ol 
• 955951-03-8 (R)-ethyl 4-anilinoxy-5-phenylpent-2-enoate 
• 104-53-0 3-phenyl-propionaldehyde 
• 955951-04-9 (S)-ethyl 4-hydroxy-5-phenylpentanoate 
• 924893-87-8 4-hydroxy-N,N-dimethyl-5-phenylpentanamide 

Downstream Products

• 203243-30-5 3-hydroxy-5-phenylmethyl-(3R,5R)-tetrahydrofuran-2-one 

Relevant academic research and scientific papers

Carboxyl Group-Directed Iridium-Catalyzed Enantioselective Hydrogenation of Aliphatic ?-Ketoacids

Although the transition metal-catalyzed asymmetric hydrogenation of aromatic ketones has been extensively explored, the enantioselective hydrogenation of aliphatic ketones remains a challenge because chiral catalysts cannot readily discriminate between the re and si faces of these ketones. Herein, we report a carboxyl-directing strategy for the asymmetric hydrogenation of aliphatic ?-ketoacids. With catalysis by iridium complexes bearing chiral spiro phosphino-oxazoline ligands, hydrogenation of aliphatic ?-ketoacids afforded chiral ?-hydroxylacids with high enantioselectivity (up to 99% ee). Mechanistic studies revealed that the carboxyl group of the substrate directs hydrogen transfer and ensures high enantioselectivity. Density functional theory calculations suggested the occurrence of chiral induction involving a hydrogen-hydrogen interaction between a hydride on the iridium atom and the substituent on the oxazoline ring of the ligand, and on the basis of the calculations, we proposed a catalytic cycle involving only Ir(III), which differs from the Ir(III)/Ir(V) catalytic cycle that operates in the hydrogenation of α,β-unsaturated carboxylic acids.

Ir-Catalyzed Asymmetric Hydrogenation of α-Alkylidene β-Lactams and Cyclobutanones

Chiral β-lactams and cyclobutanones are present in numerous natural and pharmaceutical products. The stereoselective construction of chiral four-membered cyclic compounds is an ongoing challenge for the chemical community. Herein, we report a highly stere

Preparation of optically active 4-substituted γ-lactones by lipase-catalyzed optical resolution

Optically active 4-substituted γ-lactones (3 and 4) were synthesized effectively using lipase-catalyzed optical resolution. N-methyl-4-hydroxyalkanamides (rac-1a-i) as substrates were prepared from N-methylsuccinimide. The alkylation of N-methylsuccinimid

Efficient synthesis of γ-lactones via gold-catalyzed tandem cycloisomerization/oxidation

A novel Au-catalyzed tandem cycloisomerization/oxidation of homopropargyl alcohols was developed. Various γ-lactones can be accessed readily by utilizing this strategy. Notably, the mechanism of this reaction is distinctively different from the related Ru-catalyzed reactions where the ruthenium vinylidene intermediate was proposed.

Efficient synthesis of γ-lactones via gold-catalyzed tandem cycloisomerization/oxidation

A novel Au-catalyzed tandem cycloisomerization/oxidation of homopropargyl alcohols was developed. Various γ-lactones can be accessed readily by utilizing this strategy. Notably, the mechanism of this reaction is distinctively different from the related Ru-catalyzed reactions where the ruthenium vinylidene intermediate was proposed.

Lipase-catalyzed kinetic resolution of 2-phenylethanol derivatives and chiral oxa-Pictet-Spengler reaction as the key steps in the synthesis of enantiomerically pure tricyclic amines

A series of 5,6,7,8,9,10-hexahydro-5,9-epoxybenzocycloocten-6-amines have been synthesized and pharmacologically evaluated in receptor binding studies (σ1, σ2, NMDA, κ, and μ receptors). The first key step of the synthesis was a chir

Enantioselective synthesis of syn / anti -1,3-amino alcohols via proline-catalyzed sequential α-aminoxylation/α-amination and horner-wadsworth-emmons olefination of aldehydes

(Figure presented) A novel and general method for asymmetric synthesis of both syn/anti-1,3-amino alcohols is described. The method uses proline-catalyzed sequential α-aminoxylation/ α-amination and Horner-Wadsworth-Emmons (HWE) olefination of aldehydes as the key step. By using this method, a short synthesis of a bioactive molecule, (R)-1-((S)-1-methylpyrrolidin-2-yl)-5- phenylpentan-2-ol, is also accomplished.

Asymmetrie direct vinylogous aldol reaction of furanone derivatives catalyzed by an axially chiral guanidine base

Ace of Base: The first highly enantioselectlve direct vinylogous aldol reaction of dihalogenated or α-thio-substituted furanones with aldehydes utilizes an axially chiral guanidine base catalyst. The method provides facile access to enantioenriched γ-subs

Iterative approach to enantiopure synlanti-1,3-polyols via proline-catalyzed sequential a-aminoxylation and horner-wadsworth-emmons olefination of aldehvdes

Iterative use of proline-catalyzed tandem α-aminoxylation and HWE olefination of aldehydes provided a simple access to 1,3-polyols. The feasibility of this approach is initially studied to synthesize syn- and anti-1,3-diols and is further extended to a syn/syn-1,3,5-triol at a useful level of asymmetric induction and yield. Its usage is illustrated by the short synthesis of a hydroxylactone pheromone component, (2S,3S)-2- hydroxyhexylcyclopentanone.

A short synthesis of (+)-harzialactone A and (R)-(+)-4-hexanolide via proline-catalyzed sequential α-aminooxylation and Horner-Wadsworth-Emmons olefination of aldehydes

An efficient and short enantioselective synthesis of the antitumor marine metabolite, (+)-harzialactone A 1 and pheromone, (R)-(+)-4-hexanolide 2 using l-proline-catalyzed sequential α-aminooxylation and Horner-Wadsworth-Emmons olefination of the respecti