118133-69-0

Upstream product

• 30414-58-5 methyl 3-oxo-5-phenylpentanoate 
• 104-53-0 3-phenyl-propionaldehyde 
• 36850-80-3 [(1-methoxyvinyl)oxy]trimethylsilane 
• 77086-38-5 ketene t-butyldimethylsilyl methyl acetal 
• 22348-97-6 methyl 3-oxotetradecanoate 
• 100-39-0 benzyl bromide 
• 768-56-9 4-Phenylbut-1-ene 
• 16695-14-0 Malonic acid monomethyl ester 
• 105-45-3 acetoacetic acid methyl ester 
• 118133-59-8 (2S)-1-<(S)-p-chlorophenylsulfinyl>-4-phenyl-2-butanol 
• 118133-49-6 (S)-1-(p-chlorophenylsulfinyl)-4-phenyl-2-butanone 
• 30568-00-4 dianion of methyl acetoacetate 
• 129880-16-6 3-hydroxy-5-phenyl-pentanoic acid methyl ester 
• 918148-53-5 (S)-3-Acetoxy-5-phenyl-pentanoic acid methyl ester 

Downstream Products

• 182950-95-4 (S)-5-hydroxy-3-oxo-7-phenyl-heptanoic acid tert-butyl ester 
• 182950-96-5 (6S)-6-(2-phenylethyl)dihydropyran-2,4⁽³⁾-dione 
• 587-63-3 7,8-dihydrokawain 

Relevant academic research and scientific papers

Asymmetric Palladium-Catalyzed Oxycarbonylation of Terminal Alkenes: Efficient Access to β-Hydroxy Alkylcarboxylic Acids

A novel PdII-catalyzed enantioselective oxycarbonylation of alkenes has been established. The ligand with an ethyl group at the C-6 position of Pyox plays a significant role in the intermolecular oxypalladation process, leading to high reactivity and excellent enantioselective control. Compared to the conventional methods, the reaction itself features alkenes as easily prepared starting materials, mild and operationally simple reaction conditions, and insensitivities to air and water. Moreover, this method allows for broad alkene substrate scope, excellent regio- and enantioselectivities, scalabilities and a wide array of applications, and provides a useful route for the convenient and straightforward synthesis of chiral β-hydroxy alkylcarboxylic acids/esters.

Ni(II)-Catalyzed Enantioselective Synthesis of β-Hydroxy Esters with Carboxylate Assistance

A Ni-oxazoline complex-catalyzed asymmetric decarboxylative aldol reaction between malonic acid half-oxyesters and various carbonyls with carboxylate assistance was developed, affording structurally diverse β-hydroxy esters with good yields and enantioselectivities under mild conditions. Importantly, the broad substrate scope of this methodology enabled rapid accesses to several natural products and their analogues as exemplified by phenylpropanoid, phaitanthrin B, and phthalide.

Synthesizing method of chiral beta hydroxyl acid ester compound

The invention discloses a synthesizing method of a chiral beta hydroxyl acid ester compound. The synthesizing method is characterized by including: subjecting an aldehyde compound and monoalkyl malonate serving as the raw materials to direct and sufficien

Chiral Surfactant-Type Catalyst: Enantioselective Reduction of Long-Chain Aliphatic Ketoesters in Water

A series of amphiphilic ligands were designed and synthesized. The rhodium complexes with the ligands were applied to the asymmetric transfer hydrogenation of broad range of long-chained aliphatic ketoesters in neat water. Quantitative conversion and excellent enantioselectivity (up to 99% ee) was observed for α-, β-, γ-, δ- and ε-ketoesters as well as for α- and β-acyloxyketone using chiral surfactant-type catalyst 2. The CH/π interaction and the strong hydrophobic interaction of long aliphatic chains between the catalyst and the substrate in the metallomicelle core played a key role in the catalytic transition state. Synergistic effects between the metal-catalyzed site and the hydrophobic microenvironment of the core in the micelle contributed to high stereoselectivity. (Chemical Equation Presented).

Chemoenzymatic synthesis of enantiomerically enriched kavalactones

Lipase-mediated kinetic resolution of methyl-3-hydroxy-5-phenylpentanoate and (6E)-ethyl 5-hydroxy-3-oxo-7-phenylhept-6-enoate is described in high enantiomeric excess and good yields. The effect of different lipases in different solvents has been screened using different acylating agents. This protocol has been extended for the preparation of enantiomerically pure biologically important kavalactones.

Lewis base activation of Lewis acids: Catalytic, enantioselective addition of silyl ketene acetals to aldehydes

The concept of Lewis base activation of Lewis acids has been reduced to practice for catalysis of the aldol reaction of silyl ketene acetals and silyl dienol ethers with aldehydes. The weakly acidic species, silicon tetrachloride (SiCl4), can b

Enantioselective synthesis of α-amino acids from N-tosyloxy β-lactams derived from β-keto esters

A novel synthetic sequence has been developed to convert simple β-keto esters into enantiomerically enriched α-amino acids. The key features of this sequence include the addition of azide to the C3 position of β-keto ester derived N-tosyloxy-β-lactams through a concomitant nucleophilic addition/N-O bond reduction reaction, a mild CsF-induced N1 benzylation of α-azido monocyclic β-lactams, the preparation of α-keto-β-lactams through a novel four-step sequence from the corresponding 3-azido-1-benzyl-β-lactams, and TEMPO-mediated ring expansion of these compounds to the corresponding N-carboxy anhydrides (NCAs). In addition, the synthesis, isolation, and characterization of unusual 3-imino and 3-chloramino-β-lactams is reported.

Lewis base activation of Lewis acids. Addition of silyl ketene acetals to aldehydes

The weak Lewis acid silicon tetrachloride can be activated by catalytic amounts of the chiral bisphosphoramide (R,R)-3 to form a highly reactive, chiral trichlorosilyl cation which is an extremely effective promoter of aldol addition reactions between ald

Phenylvaleric acid and flavonoid glycosides from Polygonum salicifolium

(3R)-O-β-D-Glucopyranosyloxy-5-phenylvaleric acid (1), (3R)-O-β-D- glucopyranosyloxy-5-phenylvaleric acid n-butyl ester (2), and a new dihydrochalcone diglycoside 4'-O-[β-D-glucopyranosyl-(1→-6)- glucopyranosyl]-oxy-2'-hydroxy-3',6'-dimethoxydihydrochalco

An in situ procedure for catalytic, enantioselective acetate aldol addition. Application to the synthesis of (R)-(-)-epinephrine

We report an in situ preparation of catalyst 3 which substantially simplifies the experimental procedure for the enantioselective, catalytic acetate aldol addition reaction. The addition of Me3SiCl and Et3N circumvents the azeotropic removal of the released isopropanol upon treating ligands 1 and 2 with Ti(O(i)Pr)4. Importantly, this new procedure maintains the salient features of the catalytic process we originally described: high yields and enantioselectivities, low catalyst loads, and convenient reaction times and temperatures. We have applied the new procedure to an efficient synthesis of (R)-(-)-epinephrine from commercially available reagents in an overall yield of 45%.