112607-22-4

Upstream product

• 22187-89-9 4-oxo-6-phenylhexanoic acid methyl ester 
• 90147-73-2 ethyl 4-oxo-6-phenylhexanoate 
• 13122-67-3 6-phenyl-4-oxohexanoic acid 
• 103-63-9 1-phenyl-2-bromoethane 
• 69485-62-7 3-phenyl-1-propylidenecyclopropane 

Downstream Products

• 138298-28-9 Acetic acid (R)-4-hydroxy-6-phenyl-hexyl ester 
• 138298-28-9 Acetic acid (S)-4-hydroxy-6-phenyl-hexyl ester 
• 138298-29-0 Acetic acid (S)-1-phenethyl-butyl ester 
• 138298-29-0 Acetic acid (R)-1-phenethyl-butyl ester 
• 134627-14-8 (+)-1-Phenyl-hexan-3-ol 
• 303191-35-7 (R)-1-phenylhexan-3-ol 
• 31323-51-0 (S)-γ-Propyl-γ-butyrolactone 
• 2429-96-1 2-(2-phenylethyl)tetrahydrofuran 
• 138298-27-8 (S)-6-Phenyl-hexane-1,4-diol 
• 2430-76-4 (R)-6-Phenyl-hexane-1,4-diol 
• 114361-75-0 (R,E)-5-styryldihydrofuran-2(3H)-one 
• 138381-24-5 (S,E)-5-styryldihydrofuran-2(3H)-one 

Relevant academic research and scientific papers

Process-scale preparation of enantiomerically pure γ-lactones by asymmetric hydrogenation of γ-ketoesters and comparative tests of the sensory properties of some antipodes

A reliable methodology, applicable on a process-scale level, for producing enantiomerically pure chiral γ-lactones by enantioselective hydrogenation of γ-ketoesters, followed by cyclisation of the resulting γ-hydroxyesters, has been developed. The multi-step procedure was transformed into a one-pot reaction. A very efficient chiral Ru-complex, based on the biheteroaromatic diphosphine ligand tetraMe-BITIOP, was developed as a catalyst, capable of coupling fast kinetics with high stereoselection levels. Its structure was fully elucidated through 31P NMR, EPR and X-ray single-crystal analyses. The optimal experimental conditions are as follows: hydrogen pressure=30psi, S/C ratio=2000, 30% in weight substrate concentration. Yields are quantitative and enantiomeric excesses in the range 98-99.9%. Sensorial tests on the antipodes of two γ-lactones demonstrated the very different properties of the enantiomers.

Palladium/Zinc Co-Catalyzed Asymmetric Hydrogenation of γ-Keto Carboxylic Acids

A palladium-catalyzed asymmetric hydrogenation of levulinic acid has been successful developed by using Zn(OTf)2 as co-catalyst. The present method not only has provided a strategy in the palladium-catalyzed asymmetric hydrogenation of ketone, but also allowed the preparation of a wide range of chiral γ-valerolactones in good yields with excellent enantioselectivities.

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.

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

Catalytic enantioselective synthesis of 2-alkylcyclobutanones and 4-alkyl-γ-butyrolactones from alkylidenecyclopropanes and the Sharpless AD-mix reagent

Reaction of AD-mix with alkylidenecyclopropanes allows the synthesis of optically active 2-alkylcyclobutanones and 4-alkyl-γ-butyrolactones after stepwise pinacolic rearrangement and Beyer-Villiger oxidation.

Baker's yeast reduction of arylalkyl and arylalkenil γ- and δ-keto acids

γ- and δ-Lactones 5, 6, 13, 14, 15 and 16 were synthesized via baker's yeast reduction of the corresponding keto acids 3, 4 and 9-12. The enantioselectivity of the reduction is strongly dependent on the nature of the keto acid; the δ-lactones ware always obtained in an ee% higher than the γ-lactones and ranging from 70% to 100%.