111138-02-4

Upstream product

• 6270-17-3 ethyl 3-benzoylpropanoate 
• 112635-79-7 (-)-(S)-methyl 4-(dimethyl-t-butylsilyloxy)-4-phenylbutanoate 
• 2051-95-8 succinylbenzene 
• 34674-93-6 4-hydroxy-4-phenylbutanoic acid 
• 24241-74-5 (+/-)-4-hydroxy-4-phenylbutanenitrile 
• 176850-44-5 4-Oxo-4-phenyl-butyric acid (2S,3R,3aS,6R,6aR)-2-benzyloxy-6-hydroxy-hexahydro-furo[3,2-b]furan-3-yl ester 
• 87768-37-4 ethyl 4-phenyl-4-[(trimethylsilyl)oxy]butanoate 
• 4850-50-4 1-phenyl-butane-1,4-diol 
• 58518-86-8 4-nitro-1-phenylbutan-1-one 
• 53917-82-1 β-benzoylpropionyl chloride 
• 33401-74-0 ethyl (3R)-3-hydroxy-3-phenylpropionate 
• 1020690-38-3 (S)-3-benzoyl-N-(α-phenylethyl)propanamide 
• 25333-24-8 3-benzoylpropionic acid methyl ester 
• 39755-03-8 4-hydroxy-1-phenyl-butan-1-one 

Downstream Products

• 4850-50-4 (S)-(-)-1-Phenylbutane-1,4-diol 

Relevant academic research and scientific papers

Biotransformation of aromatic ketones and ketoesters with the non-conventional yeast Pichia glucozyma

The non-conventional yeast Pichia glucozyma CBS 5766 has been used for the biotransformation of different aromatic ketones and ketoesters. The growth and biotransformation conditions were optimised for the reduction of acetophenone and under optimised conditions, propiophenone, butyrophenone and valerophenone were reduced to the corresponding (S)-alcohols with high yields and enantioselectivity. Ketoreductase(s) of Pichia glucozyma showed high catalytic activities also towards aromatic β- and γ-ketoesters, being often competitive with esterase(s). These concurrent activities allowed for the preparation of hydroxyesters, hydroxyacids and lactones often in a very selective manner.

Strain Release of Donor-Acceptor Cyclopropyl Boronate Complexes

The reactivity of boronate complexes which resemble donor-acceptor cyclopropanes is described. The enantioenriched cyclopropyl boronate complexes were shown to undergo concerted 1,2-metalate rearrangement/ring opening upon activation with a Lewis acid. Th

Bakers' yeast reduction of γ and δ ketonitriles: Intermediates for the synthesis of (S)-5-hexanolide and other chiral lactones

A number of γ and δ ketonitriles have been synthesized and their reduction with bakers' yeast carefully studied. Both 4-oxopentanenitrile and 5-oxohexanenitrile are reduced in moderate yields to the corresponding (S) alcohols of high ee while other substrates gave products of varying optical purities. These alcohols are useful intermediates for the preparation of chiral lactones, including the synthetically important (S)(-)-4-methylbutyrolactone and (S)-5-hexanolide.

Influence of Helical Structure on Chiral Recognition of Poly(phenylacetylene)s Bearing Phenylcarbamate Residues of L -Phenylglycinol and Amide Linage as Pendants

Four poly(phenylacetylene)s (PPA-1, PPA-2, PPA-3, PPA-4) bearing phenylcarbamate residues of L-phenylglycinol and amide linkage as pendants were prepared to be used as chiral stationary phases (CSPs) for high-performance liquid chromatography (HPLC), and the influences of coating solvents, dimethylformamide (DMF) and tetrahydrofuran (THF), which were used for coating the polymers on silica gel, on the helical structure of the polymers and their chiral recognition abilities were investigated. The structure analysis of PPA-1, PPA-2, PPA-3, PPA-4 by 1H nuclear magnetic resonance (NMR), size exclusion chromatography (SEC), optical rotation, and circular dichroism (CD) spectra indicated that the polymers possess the cis-transoidal structure with dynamic helical conformation. The polymers in THF seem to have shorter conjugated helical main chains along with a tighter twist conformation than those in DMF. The chiral recognition abilities of PPA-1, PPA-2, PPA-3, PPA-4 with the different helical structures induced by the coating solvents were evaluated as the CSPs in HPLC. The helical structures of PPA-1, PPA-2, PPA-3, PPA-4 induced with THF are preferable for chiral recognition for some racemates compared to those induced with DMF, and higher chiral recognition abilities of PPA-1, PPA-2, PPA-3, PPA-4 were achieved using THF.

A convenient route to optically active γ-substituted γ-lactones

Sodium borohydride reduction of 4-substituted (-)-menthyl/ (-)-bornyl-4-oxobutanoates followed by simple trituration in acidic medium at low temperature resulted in the formation of optically active γ-substituted γ-lactones.

Enantioselective synthesis of 4-substituted γ-lactones

BINAP-Ru(II) catalyzed hydrogenation of prochiral 4-oxo carboxylic esters and o-acylbenzoates gives either enantiomer of the corresponding γ-lactones in >98% enantiomeric excesses.

Efficient intramolecular asymmetric reductions of α-, β-, and γ-keto acids with diisopinocampheylborane1

(equation presented) α-, β-, and γ-Keto acids are reduced with diisopinocampheylborane at room temperature to the corresponding hydroxy acids with predictable stereochemistry in very high ee. The γ-hydroxy acids produced were conveniently cyclized to the corresponding lactones. This provides a simple synthesis of 4-hexanolide, a component of the pheromone secreted by the female dermestid beetle Trogoderma glabrum.

Syntheses of a flobufen metabolite and dapoxetine based on enantioselective allylation of aromatic aldehydes

The enantioselective allylation of an aromatic aldehyde to give a chiral homoallylic alcohol was employed as the key step in the syntheses of a flobufen metabolite and dapoxetine. In the former case, the homoallylic alcohol moiety (99 % ee) was converted into a five-membered lactone ring with good preservation of the optical purity, and the target compound, a flobufen metabolite, was obtained in 95 % ee. In the latter case, the homoallylic alcohol moiety (97 % ee) was transformed over several steps into a 3-aminopropanol moiety. During the course of the synthesis, the gradual loss of optical purity was observed, and the target compound, dapoxetine, was obtained in 85 % ee. The enantioselective allylation of an aromatic aldehyde to give the corresponding homoallylic alcohol was the key step in the syntheses of a flobufen metabolite and dapoxetine. In the first case, the homoallylic moiety was converted into a chiral five-membered lactone ring. In the second case, it was transformed into a chiral 1,3-amino alcohol moiety. Copyright

Nickel-Catalyzed Asymmetric Hydrogenation of γ-Keto Acids, Esters, and Amides to Chiral γ-Lactones and γ-Hydroxy Acid Derivatives

A highly efficient asymmetric hydrogenation of a series of γ-keto acid derivatives, including γ-keto acids, esters, and amides, using a Ni-(R,R)-QuinoxP? complex as the catalyst has been developed to afford chiral γ-hydroxy acid derivatives with excellent enantioselectivities, up to 99.9% ee. This method provides not only an economical one-pot approach for the synthesis of chiral γ-lactones but also access to (S)-norfluoxetine, an inhibitor of neural serotonin reuptake and an essential intermediate for pharmaceutical synthesis.

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.