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Upstream product

• 1823-54-7 α-methyl-β-propiolactone 
• 100-51-6 benzyl alcohol 
• 72657-23-9 methyl (R)-3-hydroxy-2-methylpropionate 
• 385817-43-6 2-hydroxymethylacrylic acid benzyl ester 
• 100-39-0 benzyl bromide 

Relevant academic research and scientific papers

Chemoenzymatic Hydroxymethylation of Carboxylic Acids by Tandem Stereodivergent Biocatalytic Aldol Reaction and Chemical Decarboxylation

Chiral 2-substituted 3-hydroxycarboxylic acid derivatives are valuable building blocks for the preparation of naturally occurring and synthetic biologically active molecules. Current methodologies for the preparation of these compounds are still limited f

Asymmetric synthesis of chiral Roche ester and its derivatives via Rh-catalyzed enantioselective hydrogenation with chiral phosphine-phosphoramidite ligands

Methyl 3-hydroxy-2-methylpropionate, known as the Roche ester, was prepared with high enantioselectivity (up to 96.7% ee) via the Rh-catalyzed asymmetric hydrogenation of methyl 2-hydroxymethylacrylate with a chiral 1,2,3,4-tetrahydro-1-naphthylamine-deri

Highly enantioselective synthesis of 3-hydroxy-2-methylpropanoic acid esters through ruthenium-SYNPHOS-catalyzed hydrogenation: Useful building blocks for the synthetic community

Both enantiomers of 3-hydroxy-2-methylpropanoic acid tert-butyl ester were prepared with high enantioselectivity (up to 94%) through a ruthenium- SYNPHOS-promoted asymmetric hydrogenation reaction using an atom-economic transformation from simple and inexpensive precursors.

Switching Lysophosphatidylserine G Protein-Coupled Receptor Agonists to Antagonists by Acylation of the Hydrophilic Serine Amine

Three human G protein-coupled receptors (GPCRs)—GPR34/LPS1, P2Y10/LPS2, and GPR174/LPS3—are activated specifically by lysophosphatidylserine (LysoPS), an endogenous hydrolysis product of a cell membrane component, phosphatidylserine (PS). LysoPS consists of-serine, glycerol, and fatty acid moieties connected by phosphodiester and ester linkages. We previously generated potent and selective GPCR agonists by modification of the three modules and the ester linkage. Here, we show that a novel modification of the hydrophilic serine moiety, that is, N-acylations of the serine amine, converted a GPR174 agonist to potent GPR174 antagonists. Structural exploration of the amide functionality provided access to a range of activities from agonist to partial agonist to antagonist. The present study would provide a new strategy for the development of lysophospholipid receptor antagonists.

Asymmetric hydrogenation with highly active IndolPhos-Rh catalysts: Kinetics and reaction mechanism

The mechanism of the IndolPhos-Rh-catalyzed asymmetric hydrogenation of prochiral olefins has been investigated by means of X-ray crystal structure determination, kinetic measurements, high-pressure NMR spectroscopy, and DFT calculations. The mechanistic study indicates that the reaction follows an unsaturate/dihydride mechanism according to Michaelis Menten kinetics. A large value of KM (KM = 5.01 ± 0.16 M) is obtained, which indicates that the Rh-solvate complex is the catalyst resting state, which has been observed by high-pressure NMR spectroscopy. DFT calculations on the substrate-catalyst complexes, which are undetectable by experimental means, suggest that the major substrate-catalyst complex leads to the product. Such a mechanism is in accordance with previous studies on the mechanism of asymmetric hydrogenation reactions with C1-symmetric heteroditopic and monodentate ligands.

Singly hydrogen bonded supramolecular ligands for highly selective rhodium-catalyzed hydrogenation reactions

(Chemical Presented) H bonds make the catalyst! A single hydrogen bond between ligands coordinated to a rhodium center is critical for the formation of pure supramolecular catalyst for asymmmetric hydrogenation reactions. The ester group of the amidite ligand (see scheme) also forms a hydrogen bond with the coordinated substrate. Use of the herecomplex afforded the highest enantioselectivity reported to date for the hydrogenation of several ester substrates.

Asymmetric synthesis of the Roche ester and its derivatives by rhodium-INDOLPHOS-catalyzed hydrogenation

(S)-3-Hydroxy-2-methylpropionate, known as the Roche ester, and several of its derivatives were successfully synthesized through asymmetric rhodium-catalyzed hydrogenation, using INDOLPHOS (diisopropyl{1-[(S)-3,5-dioxa- 4-phosphacyclohepta[ 2,1-a;3,4-a′]dinaphthalen-4-yl]-3-methyl-2-indolyl} phosphine) as the chiral ligand, in excellent yield and the highest ee reported up to now (TOF over 5500 h-1 at 25°C; up to 98% ee at -40°C).

Convenient general asymmetric synthesis of roche ester derivatives through catalytic asymmetric hydrogenation: Steric and electronic effects of ligands

An efficient and concise asymmetric hydrogenation of acrylate esters promoted by the cationic ruthenium monohydride complex [Ru(H) (hη6-cot)SYNPHOS]+BF44- is reported. A full investigation of the effects of catalyst precursors, solvents, temperature, hydrogen pressure, substrates as well as steric and electronic properties of ligands was carried out. The corresponding valuable Roche ester derivatives were obtained in good to excellent isolated yields and high enantioselectivities under mild conditions. The robustness and practicability of this highly enantioselective hydrogenation was demonstrated by the synthesis of the 3-hydroxy-2-methylpropanoic acid tert-butyl ester on a multigram scale, resulting in excellent yield and ee up to 94%.

The absolute configuration of gambieric acids A-D, potent antifungal polyethers, isolated from the marine dinoflagellate Gambierdiscus toxicus

The absolute configurations of potent antifungal polyether compounds, gambieric acids A-D, isolated from the marine dinoflagellate Gambierdiscus toxicus were determined by combining the modified Mosher method, NMR analysis, and chiral fluorimetric HPLC. (C) 2000 Elsevier Science Ltd.

Lipase promoted asymmetric trans-esterification of 4-alkyl-, 3-alkyl- and 3,4-dialkyloxetan-2-ones with ring-opening

Kinetic resolution of(+/-)-4-substituted [(+/-)-1], 3-substituted [(+/-)-4] and 3,4-disubstituted oxetan-2-ones [(+/-)-7] was effected by the action of lipases in organic solvents. The substrates (+/-)-1, (+/-)-4 and (+/-)-7 were prepared by [2 + 2] cycloaddition of aldehydes with ketene, intramolecular substitution of 3-bromoalkanoic acids and the Adam's cyclization of anti- and syn-3-hydroxyalkanoic acids, respectively. Lipase PS exhibited good activity towards all the oxetanones and was employed for the resolution experiments except with (+/-)-4-methyloxetan-2-one (+/-)-1a for which PPL was used. The stereoselectivity was satisfactory for obtaining oxetan-2-ones of high ee's except for a few cases. The configuration of new compounds was established by chemical correlation and CD spectroscopy.