107643-29-8

Upstream product

• 108-05-4 vinyl acetate 
• 127913-26-2 2(R*),3-epoxy-1(S*)-phenylpropan-1-ol 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 31814-66-1 Phenyl-((R)-3-trimethylsilanyl-oxiranyl)-methanol 
• 31930-44-6 (Z)-1-phenyl-3-(trimethylsilyl)prop-2-en-1-ol 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 1137968-48-9 (1R,2R)-3-chloro-1-phenylpropane-1,2-diol 
• 2687-12-9 cinnamyl chloride 
• 4392-24-9 3-bromo-1-phenyl-1-propenyl bromide 
• 4392-27-2 trans-2-(chloromethyl)-3-phenyloxirane 
• 100-52-7 benzaldehyde 
• 5650-34-0 2,3-epoxy-1-phenylpropan-1-one 
• 24193-22-4 (+/-)-(2S,3R)-2-(bromomethyl)-3-phenyloxirane 

Downstream Products

• 6254-48-4 (2S,3R)-3-phenylserine 
• 50706-19-9 (4R,5S)-2-Oxo-5-phenyl-oxazolidine-4-carboxylic acid 
• 127913-31-9 (4S,5R)-2-oxo-5-phenyloxazolidine-4-carboxylic acid 
• 40421-51-0 (1R,2R)-1-phenylpropane-1,2-diol 
• 146388-55-8 (1R,2R)-2,3-epoxy-1-phenylpropan-1-ol 
• 693221-49-7 (1R,2R)-1-(7-fluoro-benzo[b]thiophen-4-yloxy)-3-methylamino-1-phenyl-propan-2-ol hydrochloride 
• 693220-72-3 (2S)-2-[(S)-(benzo[b]thiophen-7-yloxy)-phenyl-methyl]-oxirane 
• 127913-29-5 Benzoic acid (4R,5R)-2-oxo-5-phenyl-oxazolidin-4-ylmethyl ester 
• 40421-52-1 (1R,2S)-1-phenylpropane-1,2-diol 

Relevant academic research and scientific papers

Enzymatic Preparation of Chiral 1-Phenylglycidols and 1-Phenyl-1,2-propanediols

Asymmetric synthesis of chiral 1-phenylglycidols and the O-acetates, which were expected to be useful intermediates for the synthesis of β-blockers, has been achieved effectively by use of baker's yeast and lipase PS.These chiral epoxides could be reduced regioselectively with lithium aluminium hydride to give chiral 1-phenyl-1,2-propanediols.

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.

Vanadium-catalyzed enantioselective desymmetrization of meso secondary allylic alcohols and homoallylic alcohols

(Chemical Equation Presented) Desymmetrization isn't complex: The substrate scope for vanadium-catalyzed epoxidation has been extended. In addition to various allylic alcohols, homoallylic alcohols can also be desymmetrized by using vanadium/bishydroxamic

Development and application of versatile bis-hydroxamic acids for catalytic asymmetric oxidation

In this article, we describe the development and preliminary results of our new designed C2-symmetric bis-hydroxamic acid (BHA) ligands and the application of the new ligands for vanadium-catalyzed asymmetric epoxidation of allylic alcohols as well as homoallylic alcohols. From this success we demonstrate the versatile nature of BHA in the molybdenum catalyzed asymmetric oxidation of unfunctionalized olefins and sulfides.

Enantioselective epoxidation of allylic alcohols by a chiral complex of vanadium: An effective controller system and a rational mechanistic model

(Chemical Equation Presented) Bishydroxamic acid derivatives are used as ligands for a vanadium catalyst in the preparation of epoxy alcohols (see scheme). The methodology uses aqueous tert-butyl hydroperoxide (TBHP) as an achiral oxidant, low catalyst loading, low reaction temperatures (0°C to room temperature), and simple workup procedures. The reaction is applied to the kinetic resolution of a secondary allylic alcohol and the preparation of small epoxy alcohols. R1, R2, R3: alkyl, aryl, H.

Enantioselective synthesis of chromenes

A concise approach for the synthesis of optically active chromenes is reported. The process described herein involves, as the key steps, a Sharpless-epoxidation, a selective deoxygenation, and a ring-closing metathesis.

Divergent stereoselectivity in the reduction of α,β-epoxy ketones using hydridosilicates

α,β-Epoxy ketones are reduced by trimethoxysilane in the presence of a catalytic amount of lithium melboxide to yield the corresponding alcohols. This reaction system reveals divergent selectivity depending on the solvent; both anti-selectivity and syn-se

Novel Synthesis of syn-α,β-Epoxy Alcohols by Diastereoselective Carbonyl Reduction of α,β-Epoxy Ketones

A novel tin hydride reagent, Bu3SnH-Bu4NCN, reduced α,β-epoxy ketones to the corresponding syn-α,β-epoxy alcohols in high diastereoselectivities.

RAPID SYNTHESIS OF β-HYDROXY-α-AMINO ACIDS, SUCH AS L-THREONINE, β-HYDROXYPHENYLALANINE, AND β-HYDROXYLEUCINE, VIA AN APPLICATION OF THE SHARPLESS ASYMMETRIC EPOXIDATION

The optically active epoxy alcohols 6abc, prepared by a Sharpless kinetic resolution-epoxidation process, were converted to the optically pure β-hydroxy-α-amino acids 1abc in four steps and high overall yield.