36615-45-9

Usage

Chemical Properties

CLEAR COLORLESS VISCOUS LIQUID

InChI:InChI=1/C10H12O3/c1-13-10(12)7-9(11)8-5-3-2-4-6-8/h2-6,9,11H,7H2,1H3/t9-/m0/s1

Upstream product

• 67-56-1 methanol 
• 36567-72-3 (S)-3-hydroxy-3-phenylpropanoic acid 
• 186581-53-3 diazomethane 
• 58059-08-8 tert-butyl (R)-p-toluenesulfinylacetate 
• 100-52-7 benzaldehyde 
• 3480-87-3 3-hydroxy-3-phenylpropanoic acid 
• 63741-23-1 α-(p-tolylsulfinyl) β-hydroxy β-phenyl propionate de t-butyle 
• 614-27-7 methyl 3-oxo-3-phenylpropionate 
• 109053-85-2 methyl 3-(dimethyl(phenyl)silyl)-3-phenylpropanoate 
• 77086-38-5 ketene t-butyldimethylsilyl methyl acetal 
• 72656-47-4 ethyl (R)-3-hydroxy-3-phenylpropanoate 
• 591-51-5 phenyllithium 
• 109053-73-8 (3aS,6R,7aR)-8,8-dimethyl-1-[(2E)-3-phenylprop-2-enoyl]hexahydro-3a,6-methano-2,1-benzisothiazole 2,2-dioxide 
• 96-32-2 bromoacetic acid methyl ester 

Downstream Products

• 96854-34-1 (S)-3-phenyl-1,3-propanediol 
• 79-20-9 acetic acid methyl ester 
• 100-52-7 benzaldehyde 
• 96854-37-4 C₉H₁₁⁽²⁾HO 
• 96895-62-4 (R)-<3-(2)H1>-3-phenylpropionic acid 
• 96854-35-2 2,2-Dimethyl-propionic acid (S)-3-hydroxy-3-phenyl-propyl ester 
• 96854-36-3 2,2-Dimethyl-propionic acid (S)-3-chloro-3-phenyl-propyl ester 
• 96853-97-3 C₁₆H₁₄⁽²⁾HNO₂ 
• 96901-43-8 C₉H₇⁽²⁾HN₂O₆ 
• 96853-98-4 C₂₀H₂₀⁽²⁾HNO₄ 

Relevant academic research and scientific papers

On the mechanism of Lewis base catalyzed aldol addition reactions: Kinetic and spectroscopic investigations using rapid-injection NMR

The mechanistic foundations of the Lewis base catalyzed aldol addition reactions have been investigated. From a combination of low-temperature spectroscopic studies (29Si and 31P NMR) and kinetic analyses using a rapid-injection NMR apparatus (RINMR), a correlation of the ground states and transition structures for the aldolization reactions has been formulated. The aldol addition of the tert-butylsilyl ketene acetal of tert-butyl propanoate with 1-naphthaldehyde is efficiently catalyzed by a combination of silicon tetrachloride and chiral phosphoramide Lewis bases. The rates and selectivities of the aldol additions are highly dependent on the structure of the Lewis bases: bisphosphoramides give the highest rate and selectivity, whereas a related monophosphoramide reacts slowly and with low selectivity. The monophosphoramide shows no nonlinear behavior. All of the additions show a first-order kinetic dependence on silyl ketene acetal and 1-naphthaldehyde and a zeroth-order dependence on silicon tetrachloride. The kinetic order in catalyst is structure dependent and is either half-, two-thirds-, or first-order. All of the phosphoramides are saturated with silicon tetrachloride in some form, and the resting-state species are mixtures of monomeric and dimeric, pentacoordinate cationic, or hexacoordinate neutral complexes. These data allow the formulation of a unified mechanistic scheme based on the postulate of a common reactive intermediate for all catalysts.

Planar-chiral ferrocene-based triazolylidene copper complexes: Synthesis, characterization, and catalysis in asymmetric borylation of α,β-unsaturated ester

1,2,3-Triazol-5-ylidenes have recently attracted considerable attention as versatile ligands because of their strong electron-donating properties and structural diversities. While some efforts have been devoted to the development of chiral triazolylidene-

Iridium-catalyzed asymmetric hydrogenation of β-keto esters with new phenethylamine-derived tridentate P,N,N-ligands

A new class of phenethylamine-derived tridentate P,N,N-ligands has been successfully developed. These ligands exhibited good performance in the Ir-catalyzed asymmetric hydrogenation of β-keto esters, affording the corresponding β-hydroxy esters in moderat

On the basis of the phenethylamine skeleton chiral P, N, N ligand compound and its manufacturing method and application (by machine translation)

The present invention provides a chiral P based on the skeleton of the phenethylamine, N, N ligand compound and its manufacturing method and application, surfactant-ethylamine skeleton chiral P, N, N ligand compound of preparation method is as follows: under the protection of nitrogen, the chiral phenylethylamine - [...] compound with 2 - chloromethyl oxazole oxazoline compounds soluble in the reaction solvent, adding alkali, reflux reaction, filtering, desolvation, column chromatography to obtain the required chiral P, N, N ligand compound. In particular to the β - ketoacid ester compound in asymmetric catalytic hydrogenation reaction. The invention of the phenethylamine skeleton chiral P, N, β - keto ester N ligand can be applied to the asymmetric catalytic hydrogenation reaction, can be high yield and high enantio-selectively for the preparation of chiral β - hydroxy ester. (by machine translation)

Efficient Access to Chiral β-Borylated Carboxylic Esters via Rh-Catalyzed Hydrogenation

Rh/bisphosphine?thiourea ligand (ZhaoPhos)-catalyzed asymmetric hydrogenation of (Z)-β-substituted-β-boryl-α,β-unsaturated esters was successfully developed, furnishing a variety of chiral β-borylated carboxylic esters with high yields and excellent enantioselectivities (up to 99% yield and >99% ee). The gram-scale asymmetric hydrogenation was performed efficiently in the presence of only 0.05 mol% (S/C=2 000) catalyst loading with full conversion, 99% yield and 99% ee. Moreover, the hydrogenation product was easily converted to other versatile synthetic intermediates, such as methyl (S)-3-hydroxy-3-phenylpropanoate and methyl (S)-3-(furan-2-yl)-3-phenylpropanoate. (Figure presented.).

Chiral Bicyclic NHC/Cu Complexes for Catalytic Asymmetric Borylation of α,β-Unsaturated Esters

The potential of using chiral bicyclic NHC ligands that exhibit modularity was investigated in the Cu-catalyzed asymmetric borylation reaction of α,β-unsaturated esters. After screening for ligands and optimization of the reaction conditions, the corresponding products were afforded with good enantioselectivities (up to 85% ee).

Chiral Nitroarenes as Enantioselective Single-Electron-Transfer Oxidants for Carbene-Catalyzed Radical Reactions

A new class of chiral oxidants is developed. These readily accessible oxidants contain a nitro group for oxidation and a chiral sulfonamide moiety for stereoselectivity control. The chiral information from the oxidants can effectively transfer to the substrates in carbene-catalyzed β-hydroxylation of enals via single-electron-transfer radical processes. We expect these oxidants to find unique applications in other asymmetric oxidations and oxygen-atom-transferring reactions.

Iridium-catalyzed asymmetric hydrogenation of β-keto esters with f-amphox ligands

The iridium-catalyzed asymmetric hydrogenation of β-keto esters with chiral tridentate P,N,N-ligands (f-amphox) has been developed. Under the optimized conditions, a wide range of β-keto esters can be hydrogenated smoothly, affording the corresponding β-hydroxy esters in good to excellent enantioselectivities (up to 95% ee).

Method for preparing chiral beta-hydroxy ester by Ir-catalyzed asymmetric hydrogenation

The invention provides a method for preparing a chiral beta-hydroxy ester compound by Ir-catalyzed asymmetric hydrogenation. The method for preparing the chiral beta-hydroxy ester compound comprises the steps as follows: in a glove box filled with nitrogen, [Ir(COD)Cl]2 and a chiral P, N, N ligand are dissolved in anhydrous methanol, stirring is performed at room temperature for 1 hour, and a Ir catalyst is generated; substrate beta-ketoester and a base additive are added, the mixture is placed in an autoclave and hydrogenated under certain reaction pressure; hydrogen gas is slowly released, separation with a silica gel column is performed after a solvent is removed, and product beta-hydroxy ester is obtained. The reaction for preparing chiral beta-hydroxy ester by Ir-catalyzed asymmetrichydrogenation of beta-ketoester has the advantages that conditions are mild, operation is easy, enantioselectivity of the product is high and the like.

Ir-catalyzed asymmetric hydrogenation of β-keto esters with chiral ferrocenyl P,N,N-ligands

The Ir-catalyzed asymmetric hydrogenation of β-keto esters with chiral ferrocenyl P,N,N-ligands has been developed. Under the optimized conditions, a wide range of β-keto esters were hydrogenated to afford the corresponding β-hydroxy esters in good to excellent enantioselectivities (up to 95% ee).