184046-30-8

Upstream product

• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 4392-27-2 trans-2-(chloromethyl)-3-phenyloxirane 
• 98819-68-2 3-phenyl-(2R,3R)-oxiran-2-ylmethanol 

Downstream Products

• 4187-87-5 1-phenylprop-2-yn-1-ol 
• 918656-68-5 2-(N-benzyl-N-(((2R,3R)-3-phenyloxiran-2-yl)methyl)amino)ethanol 
• 655240-39-4 (1S,2S)-3-chloro-1-phenylpropane-1,2-diol 
• 139165-55-2 (2S,3R)-1-chloro-3-phenylpropane-2,3-diol 

Relevant academic research and scientific papers

Exploring substrate scope of Shi-type epoxidations

Enantioselective epoxidations of alkenes (12 examples) were achieved using a Shi-type carbohydrate-derived hydrate and Oxone. The chiral platform provided by the catalyst tolerates a wide range of substituents providing high yields and enantioselectivities (80-95.5% ee). However, styrene derivatives were only converted with poor selectivities (11-26% ee). Georg Thieme Verlag Stuttgart.

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.

The first stereoselective and the total synthesis of Leiocarpin C and total synthesis of (+)-Goniodiol

The synthesis of the styryl lactone Leiocarpin C has been achieved in a highly stereoselective manner using Jacobsen's kinetic resolution, Sharpless asymmetric epoxidation and Sharpless asymmetric dihydroxylation as key steps. This is the first total synthesis of Leiocarpin C, and thus establishes for the first time the absolute stereochemistry of this natural product.

NOREPINEPHRINE TRANSPORTER RADIOTRACERS AND METHODS OF SYNTHESES THEREOF

The present invention provides compounds and radiotracers thereof for locating, diagnosing, identifying, evaluating, detecting or quantitating NET by in vivo imaging. The invention also provides methods for locating, diagnosing, identifying, evaluating, detecting or quantitating NET, using radiotracers of high-affinity or labeled compounds of the invention, which exhibit low toxicity, can cross the blood-brain barrier and, preferably, distinguish among normal and abnormal brains. For example, a radiotracer of the invention can be administered to a patient in an amount suitable for in vivo imaging thereof. Preferably, radiotracers of the invention can also be used to locate, diagnosis, identify, evaluate, detect and quantitate NET in such diseases, disorders, conditions or maladies as, without limitation, depression, anxiety, ADHD and drug dependency.

Catalytic asymmetric epoxidation

A compound and method for producing an enantiomerically enriched epoxide from an olefin using a chiral ketone and an oxidizing agent is disclosed.

Enantioselective epoxidation of trans-disubstituted alkenes by D2-symmetric chiral dioxoruthenium(VI) porphyrins

A series of D2-symmetric chiral trans-dioxoruthenium(VI) porphyrins can effect enantioselective epoxidation of trans-β-methylstyrene in up to 70% ee, and 76% ee is attained for the oxidation of cinnamyl chloride; the facial selection for the tr

A Class of C2 and Pseudo C2 Symmetric Ketone Catalysts for Asymmetric Epoxidation. Conformational Effect on Catalysis

A class of C2 and pseudo C2 symmetric ketones with one fused ring at each side of the carbonyl group have been prepared from quinic acid and found to be effective catalysts for the asymmetric epoxidation of a variety of olefins. Electron deficient olefins such as enones can be efficiently epoxidized. Encouragingly good enantioselectivity is also obtained for the epoxidation of styrenes. The studies show that the ketone conformation plays an important role in the reactivity and selectivity of the catalyst.

An efficient catalytic asymmetric epoxidation method

This article describes a highly effective catalytic asymmetric epoxidation method for olefins using,potassium peroxomonosulfate (Oxone, Dupont) as oxidant and a fructose-derived ketone(l) as catalyst. High enantioselectivies have been obtained-for trans-disubstituted and trisubstituted olefins which can bear functional groups such as tributylsilyl ether, acetal, chloride, and ester. The enantiomeric excesses cis-olefins and terminal olefins are not high yet. The current epoxidation shows that the catalyst efficiency is enhanced dramatically-upon raising the pH. Mechanitic studies show that the epoxidation mainly proceeds via a spiro transition state, which provides a model for predicting the stereochemical outcome of the reaction. The planar transition state, likely to be the main competing pathway. The extent of the involvement of the planar mode is subject to the steric of the alkyl groups on the olefins.