130605-53-7

Upstream product

• 100-52-7 benzaldehyde 
• 105-39-5 chloroacetic acid ethyl ester 
• 146452-39-3 (2S,3R) ethyl 2-chloro-3-hydroxy-3-phenylpropionate 
• 146452-40-6 (2R,3R) ethyl 2-chloro-3-hydroxy-3-phenylpropionate 
• 757232-69-2 (2R,3R)-ethyl 2-bromo-3-hydroxy-3-phenylpropanoate 
• 757232-73-8 (2R,3R)-ethyl 3-hydroxy-2-iodo-3-phenylpropanoate 
• 77-76-9 2,2-dimethoxy-propane 
• 2272-55-1 ethyl trans-3-phenyl-1-oxirane-2-carboxylate 
• 103-36-6 ethyl 3-phenyl-2-propenoate 
• 121-39-1 ethyl 3-phenylglycidate 
• 4610-69-9 (Z)-ethyl cinnamate 
• 41381-97-9 ethyl 2-chloro-3-oxo-3-phenylpropionate 
• 105-36-2 ethyl bromoacetate 
• 623-73-4 diazoacetic acid ethyl ester 

Downstream Products

• 126060-73-9 ethyl (2R,3R)-3-phenyl-2,3-oxiranepropanoate 
• 870287-36-8 (4R,5S)-2,4-Diphenyl-4,5-dihydro-oxazole-5-carboxylic acid ethyl ester 
• 153433-81-9 syn-(2S,3R)-(+)-N-benzoyl-3-phenylisoserine ethyl ester 
• 24290-27-5 (2-nitro-phenylsulfanyl)-acetic acid ethyl ester 
• 30825-24-2 2-Hydroxy-3-(2-nitro-phenylsulfanyl)-3-phenyl-propionic acid ethyl ester 
• 19190-78-4 potassium cis-3-phenyloxiranecarboxylate 
• 18366-43-3 ethyl anti-(+/-)-2-hydroxy-3-phenyl-3-(phenylamino)propanoate 
• 119628-74-9 trans-(4S^*,5R^*)-2,2,2,4-Tetraphenyl-5-methoxycarbonyl-1,3,2-oxazaphospholidine 
• 119628-74-9 trans-(4S,5R)-2,2,2,4-Tetraphenyl-5-methoxycarbonyl-1,3,2-oxazaphospholidine 
• 119628-74-9 trans-(4R,5S)-2,2,2,4-Tetraphenyl-5-methoxycarbonyl-1,3,2-oxazaphospholidine 
• 129866-73-5 (2R,3R)-3-Phenyl-1-(3,3,3-trifluoro-2-methoxy-2-phenyl-propionyl)-aziridine-2-carboxylic acid methyl ester 
• 129866-73-5 (2S,3S)-3-Phenyl-1-(3,3,3-trifluoro-2-methoxy-2-phenyl-propionyl)-aziridine-2-carboxylic acid methyl ester 
• 129866-72-4 Methyl (2S,3R)-(-)-2-hydroxy-3-azido-3-phenyl-propionate 

Relevant academic research and scientific papers

Enantioselective bio-hydrolysis of various racemic and meso aromatic epoxides using the recombinant epoxide hydrolase Kau2

Abstract Epoxide hydrolase Kau2 overexpressed in Escherichia coli RE3 has been tested with ten different racemic and meso α,β-disubstituted aromatic epoxides. Some of the tested substrates were bi-functional, and most of them are very useful building blocks in synthetic chemistry applications. As a general trend Kau2 proved to be an extremely enantioselective biocatalyst, the diol products and remaining epoxides of the bioconversions being obtained - with two exceptions - in nearly enantiomerically pure form. Furthermore, the reaction times were usually very short (around 1 h, except when stilbene oxides were used), and the use of organic co-solvents was well tolerated, enabling very high substrate concentrations (up to 75 g/L) to be reached. Even extremely sterically demanding epoxides such as cis- and trans-stilbene oxides were transformed on a reasonable time scale. All reactions were successfully conducted on a 1 g preparative scale, generating diol- and epoxide-based chiral synthons with very high enantiomeric excesses and isolated yields close to the theoretical maximum. Thus we have here demonstrated the usefulness and versatility of lyophilized Escherichia coli cells expressing Kau2 epoxide hydrolase as a highly enantioselective biocatalyst for accessing very valuable optically pure aromatic epoxides and diols through kinetic resolution of racemates or desymmetrization of meso epoxides.

Method for Preparing Optically Pure (-)-Clausenamide Compound

Disclosed in the present invention is a method for preparing a (?)-clausenamide compound of formula (I), comprising: firstly, catalyzing the asymmetrical epoxidation of trans-cinnamate using a chiral ketone derived from fructose or a hydrate thereof as a catalyst, and then subjecting the product to transesterification, oxidation, cyclization and reduction successively to finally obtain the optically pure (?)-clausenamide compound of formula (I).

Metal-free ring-opening of epoxides with potassium trifluoroborates

The ring-opening of epoxides with potassium trifluoroborates proceeds smoothly in the presence of trifluoroacetic anhydride under metal-free conditions. The reactions are regioselective and afford a single diastereomer. Both electron-rich and electron-poor aryltrifluoroborates are tolerated.

A novel enantioselective epoxide hydrolase from Agromyces mediolanus ZJB120203: Cloning, characterization and application

A new strain Agromyces mediolanus ZJB120203, capable of enantioselective epoxide hydrolase (EH) activity was isolated employing a newly established colorimetric screening and chiral GC analysis method. The partial nucleotide sequence of an epoxide hydrolase (AmEH) gene from A. mediolanus ZJB120203 was obtained by PCR using degenerate primers designed based on the conserved domains of EHs. Subsequently, an open reading frame containing 1167 bp and encoding 388 amino acids polypeptide were identified. Expression of AmEH was carried out in Escherichia coli and purification was performed by Nickel-affinity chromatography. The purified AmEH had a molecular weight of 43 kDa and showed its optimum pH and temperature at 8.0 and 35 C, respectively. Moreover, this AmEH showed broad substrates specificity toward epoxides. In this study, it is demonstrated that the AmEH could unusually catalyze the hydrolysis of (R)-ECH to produce enantiopure (S)-ECH. Enantiopure (S)-ECH could be obtained with enantiomeric excess (ee) of >99% and yield of 21.5% from 64 mM (R,S)-ECH. It is indicated that AmEH from A. mediolanus is an attractive biocatalyst for the efficient preparation of optically active ECH.

3- and 4-uloses derived from N-acetyl- D -glucosamine: A unique pair of complementary organocatalysts for asymmetric epoxidation of alkenes

The 4-ulose and the 3-ulose, both derived in two steps from the α-methyl glycoside of N-acetyl-D-glucosamine (GlcNAc), act as organocatalysts in the asymmetric epoxidation of alkenes, with unprecedented complementary enantioselectivity. The best results are found with α,β-unsaturated esters as substrates, with enantiomeric ratios up to 90:10 and 11:89, respectively. Copyright

BOROX catalysis: Self-assembled AMINO-BOROX and IMINO-BOROX chiral Bronsted acids in a five component catalyst assembly/ catalytic asymmetric aziridination

A five-component catalyst assembly/aziridination reaction is described starting from an aldehyde, an amine, ethyl diazoacetate, B(OPh)3, and a molecule of a vaulted biaryl ligand (VAPOL or VANOL). A remarkable level of chemoselectivity was observed since, while 10 different products could have resulted from various reactions between the five components, an aziridine was formed in 85% yield and 98% ee and only two other products could be detected in 3% yield. Studies reveal that the first in a sequence of three reactions is an exceedingly rapid amine-induced assembly of an AMINOBOROX chiral Bronsted acid species from VAPOL and B(OPh)3, which is followed by imine formation from the amine and aldehyde and the concomitant formation of an IMINO-BOROX chiral Bronsted acid and finally the reaction of the imine with ethyl diazoacetate mediated by the IMINO-BOROX catalyst to give aziridine-2-carboxylic esters with very high diastereo- and enantioselectivity.

Asymmetric counteranion-directed transition-metal catalysis: Enantioselective epoxidation of alkenes with Manganese(III) salen phosphate complexes

(Figure Presented) Figure Presentation Paired up: A highly active and enantioselective ion-pair epoxidation catalyst, consisting of an achiral Mn |||-salen complex and a chiral phosphate counteranion, mediates the epoxidization of a wide range of alkenes with high yields and enantioselectivities (see scheme). The unique role of the counteranion is to stabilize an enantiomorphic conformation of the cationic Mn catalyst.

Catalytic enantioselective alkene epoxidation using novel spirocyclic N-carbethoxy-azabicyclo[3.2.1]octanones

A general synthetic route allowing access to several spirocyclic N-carbethoxy-azabicyclo[3.2.1]octanones is developed. These novel ketones efficiently catalyse alkene epoxidation using Oxone with up to 91.5% ee.

Catalytic asymmetric epoxidation of alkenes with arabinose-derived ketones containing a cyclohexane-1,2-diacetal

The effect of diol blocking groups, cyclohexane-1,2-diacetal verses butane-1,2-diacetal, on the asymmetric epoxidation of trans- and cis-alkenes by arabinose-derived ketones is reported. The ketone catalysts with a cyclohexane-1,2-acetal display similar asymmetric induction as those catalysts with a butane-1,2-diacetal in most cases. For (E)-1-benzyloxy-4-hexene, the ee of the enantioselective epoxidation has reached 61% with the cyclohexane-1,2-dineopentyl acetal ketone catalyst.

A diacetate ketone-catalyzed asymmetric epoxidation of olefins

(Chemical Equation Presented) A fructose-derived diacetate ketone has been shown to be an effective catalyst for asymmetric epoxidation. High ee values have been obtained for a variety of trans and trisubstituted olefins including electron-deficient α,β-unsaturated esters as well as certain cis olefins.