130796-40-6

Upstream product

• 103-26-4 Methyl cinnamate 
• 67-56-1 methanol 
• 81691-59-0 (2RS,3RS)-2,3-dihydroxy-3-phenyl-propionic acid methyl ester 
• 18020-59-2 methyl 3-hydroxy-2-methylidene-3-phenylpropionate 
• 100-52-7 benzaldehyde 
• 119096-73-0 methyl 3-hydroxy-2-oxo-3-phenylpropionate 
• 19190-80-8 methyl trans-3-phenylglycidate 
• 103-26-4 methyl cinnamate 
• 186581-53-3 diazomethane 
• 128822-03-7 (5S)-N-[(2E)-3-phenylprop-2-enoyl]-5-triphenylmethoxymethyl-2-pyrrolidinone 
• 130718-66-0 (R)-3-phenyl-1,1-bis(p-tolylthio)-3-(trimethylsilyloxy)propan-2-one 
• 130718-75-1 (4R,5R)-cis-4--2,2-dimethyl-5-phenyl-1,3-dioxolan 
• 130718-68-2 (R)-3-hydroxy-3-phenyl-1,1-bis(p-tolylthio)propan-2-one 
• 130718-71-7 erythro (2R,3R)-3-phenyl-1,1-bis(p-tolylthio)propane-2,3-diol 

Downstream Products

• 70159-45-4 α-(toluene-4-sulfonyloxy)-trans-cinnamic acid 
• 55568-97-3 (2R,3R)-3-hydroxyflavanone 
• 16354-93-1 (1RS,2SR)-1-phenyl-propane-1,2,3-triol 

Relevant academic research and scientific papers

Asymmetric Dihydroxylation of Olefins with a Simple Chiral Ligand

A C2 symmetrical chiral ligand derived from (R,R)-trans-1,2-diaminocyclohexane is highly effective in the asymmetric cis-dihydroxylation of aromatic and aliphatic di- and trisubstituted olefins under stoichiometric conditions.

Enantioselective synthetic method for 3-hydroxyflavanones: An approach to (2R,3R)-3',4'-O-dimethyltaxifolin

A new enantioselective synthetic method for (2R,3R)-3-hydroxyflavanone (1a) was developed via asymmetric dihydroxylation (ADH) and intramolecular Mitsunobu reaction as key reactions and the application to synthesis of (2R,3R)-3',4'-O-dimethyltaxifolin (1b) is described. (C) 2000 Elsevier Science Ltd.

Racemic or enantioselective osmium-catalyzed dihydroxylation of olefins under near-neutral conditions

K3Fe(CN)6 and NaIO4 serve as catalytic co-oxidants for osmium-catalyzed dihydroxylations that are performed under near-neutral conditions with K2S2O8 as the stoichiometric oxidant and Na2HPO4 as the base. By using either quinuclidine or hydroquinidine 1,4-phthalazinediyl ether [(DHQD)2Phal], good yields of racemic or enantioenriched diols are obtained. This simple, biphasic procedure offers advantages over other neutral dihydroxylation protocols that use N-methylmorpholine oxide as the stoichiometric oxidant, by suppressing the secondary catalytic cycle that leads to reduced enantioselectivities. The utility of the procedure, which is nicely suited for base-labile starting materials or products, is demonstrated by performing the dihydroxylation in the presence of an aliphatic aldehyde moiety.

Cis-Dihydroxylation of electron deficient olefins catalysed by an oxo-bridged diiron(III) complex with H2O2

Room temperature oxidation of olefins catalysed by a symmetrical (μ-oxo)(μ-hydroxo)diiron(III) complex (1) based on the amino pyridyl ligand bpmen (bpmen = N,N′-dimethyl-N,N′-bis(2-pyridyl methyl)ethane-1,2-diamine) with hydrogen peroxide under the conditions of limiting substrate is described. Excellent substrate conversions have been achieved under ambient reaction conditions. The olefin oxidation efficacy of the 1/H2O2 system has been found to get improved in presence of acetic acid. The catalytic system has been shown to oxidise electron-deficient olefins to the corresponding cis-diols, while epoxidation is favoured in case of electron-rich olefins. The μ-oxo diiron(III) core of the catalyst 1 has been found be regenerated after the catalytic turnovers. Addition of a second batch of substrate and oxidant at the end of the olefin oxidation results in the formation of almost identical amounts of epoxides/diols. Moreover, the regenerated catalyst exhibits a significantly higher preference towards the oxidation of electron-deficient olefins.

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.

A Morita-Baylis-Hillman adduct allows the diastereoselective synthesis of styryl lactones

We disclosed herein a diastereoselective approach for the total syntheses of (±)-Leiocarpin A and (±)-Goniodiol. These biologically active styryl lactones were obtained from a common intermediate, prepared in five steps and 40% overall yield, using a simp

Lewis base activation of Lewis acids: Catalytic enantioselective glycolate aldol reactions

(Chemical Equation Presented) Both syn- and anti-1,2-diols can be obtained with high diastereoselectivity and enantioselectivity from the properly substituted glycolate-derived silyl ketene acetals in the presence of SiCl 4 and a chiral bisphos

Sharpless asymmetric dihydroxylation of olefins in water-surfactant media with recycling of the catalytic system by membrane nanofiltration

This paper presents a new and more sustainable alternative approach for the Sharpless catalytic asymmetric dihydroxylation (AD) of olefins using a water/surfactant systemas reaction media. The AD reaction was performed using several cationic and anionic surfactants allowing yields and enantiomeric excesses higher or comparable with the conventional systems (using organic mixtures). The use of this water/surfactant medium offers the additional advantage of performing the reactions without the need of a slow addition of olefins. Asymmetric dihydroxylation of 1-hexene in a 1.5 mM sodium cholate aqueous solution, using N-methylmorpholine N-oxide (NMO) as co-oxidant was selected as model systemto evaluate the feasibility of recycling the Sharpless catalytic systemby nanofiltration. The reaction media was processed by nanofiltration, the product was isolated in the permeate, whereas the catalytic systemand surfactant were retained by the membrane and recycled through six successive reactions, improving the catalyst turn-over number. The experimental results were compared with the ones calculated on the basis of mass balances, membrane rejections to product and reaction yields.

Preparation, characterization and catalytic properties of polyaniline-supported metal complexes

Polyaniline-supported Sc, In, Pd, Os and Re catalysts were prepared by using a simple protocol and the thus prepared catalysts were well characterized using FTIR, XPS, UV-Vis/DRS, TGA-DTA. All the catalysts were successfully employed in a wide range of organic transformations such as cyanation and allylation of carbonyl compound, Suzuki coupling of aryl halides and boronic acids, and, most importantly, in asymmetric dihydroxylation of olefins to afford optically active vicinal diols. All the catalysts were separated from the reaction mixture by simple filtration and reused with consistent activity for five cycles without noticeable leaching of metal from the support.

Ruthenium- and lipase-catalyzed DYKAT of 1,2-diols: an enantioselective synthesis of syn-1,2-diacetates

Regio- and stereoselective lipase-catalyzed kinetic resolutions were investigated for some unsymmetrical, secondary/secondary syn-diols. Candida antarctica lipase B-catalyzed transesterifications of a few aryl/alkyl- and alkyl/alkyl 1,2-diols were coupled