72656-48-5

Upstream product

• 540-88-5 acetic acid tert-butyl ester 
• 100-52-7 benzaldehyde 
• 5292-43-3 bromoacetic acid tert-butyl ester 
• 63741-23-1 α-(p-tolylsulfinyl) β-hydroxy β-phenyl propionate de t-butyle 
• 51656-70-3 (2-tert-butoxy-2-oxoethyl)zinc(II) bromide 
• 54441-66-6 tert-butyl benzoylacetate 
• 74786-02-0 1-(tert-butyldimethylsilyloxy)-1-tert-butoxyethylene 
• 58059-08-8 tert-butyl (R)-p-toluenesulfinylacetate 
• 49827-15-8 t-butyl iodoacetate 
• 5397-27-3 tert-butyl 3-hydroxy-3-phenylpropionate 
• 108-24-7 acetic anhydride 
• 1760-46-9 diphenylacetic anhydride 
• 22651-87-2 cyclohexanecarboxylic acid anhydride 
• 14990-09-1 tert-butyl cinnamate 

Downstream Products

• 103548-16-9 (R)-3-phenyl-1,3-dihydroxypropane 

Relevant academic research and scientific papers

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)

PLANAR CHIRAL METALLOCENE RING-FUSED CARBENE AND PRODUCTION METHOD THEREFOR, AND METAL COMPLEX WITH THE DERIVATIVE AS LIGAND

PROBLEM TO BE SOLVED: To provide a planar chiral carbene ligand which is easily synthesized. SOLUTION: There is provided a carbene which can be synthesized from a planar chiral iminium salt derivative of the formula (1), where R1 to R9 are H, a substituted/unsubstituted C1 to C20 hydrocarbon group, a substituted/unsubstituted C1 to C20 alkoxy group, a substituted/unsubstituted C6 to C20 aryloxy group, a substituted/unsubstituted amino group, a substituted/unsubstituted phosphino group, a substituted/unsubstituted silyl group, a substituted/unsubstituted alkylthio group or a substituted/unsubstituted arylthio group or the like; X is a substituted/unsubstituted C1 to C4 carbon atom or a substituted/unsubstituted atomic group consisting of N, O, S or any combination of these hetero atoms and a carbon atom which may have a substituent; Z is a halogen atom, PF6, BF4, ClO4 or BPh4; and M is a transition atom such as Fe and Ru. Although the formula (1) represents one of two enantiomers of planar chiral compound, it may be another enantiomer. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

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.

Efficient P-Chiral Biaryl Bisphosphorus Ligands for Palladium-Catalyzed Asymmetric Hydrogenation

A series of structurally novel P-chiral biaryl bisphosphorus ligands L1-L5 (BABIBOPs) are developed, providing high efficiency for the first time in palladium-catalyzed asymmetric hydrogenation of β-aryl and β-alkyl substituted β-keto esters. With the Pd-L3 (iPr-BABIBOP) catalyst, a series of chiral β-hydroxyl carboxylic esters are formed in excellent enantioselectivities (up to>99% ee) and yields at catalyst loading as low as 0.01 mol%.

Biaryl diphosphine ligand as well as preparation method and application thereof

The invention discloses a biaryl diphosphine ligand as well as a preparation method and an application thereof. A biaryl diphosphine ligand compound represented as the formula I in the description ora biaryl diphosphine ligand enantiomer is provided, wherein R is alkyl of C1-C10 or naphthenic base of C3-C30 independently; Ra is hydrogen, alkyl of C1-C10, alkoxy of C1-C4, naphthenic base of C3-C30, halogen, R substituted or unsubstituted phenyl, R substituted or unsubstituted aryl of C10-C30 and R substituted or unsubstituted ceteroary of C4-C15 independently; all R, R and R are halogen, alkyl of C1-C4 or alkoxy of C1-C4 independently. With the adoption of the biaryl diphosphine ligand compound I, a series of chiral beta-hydroxy carboxylates with high optical purity can be effectively prepared through catalyzed synthesis, and the compound is high in economic practicability.

Planar Chiral Cyclic (Amino)(ferrocenyl)carbene as Ligand for Transition Metals

Planar chiral ferrocene-fused iminium salts were synthesized in enantiomerically pure form. The novel planar chiral cyclic (amino)(ferrocenyl)carbene successfully generated from such salt was subjected to carbene trapping experiments with sulfur and copper chloride. The utility of the carbene as a chiral ligand for transition metals was preliminarily demonstrated in the copper-catalyzed enantioselective β-boration of an α,β-unsaturated ester. (Figure presented.).

(R)-(+)-N-Methylbenzoguanidine ((R)-NMBG) catalyzed acylative kinetic resolution of racemic 3-hydroxy-3-aryl-propanoates

(R)-(+)-N-methylbenzoguanidine ((R)-NMBG) functioned as an efficient acyl transfer catalyst for the acylative kinetic resolution of racemic β-hydroxy esters using cyclohexane carboxylic anhydride under mild reaction conditions. A tert-butyl ester moiety is necessary to achieve a high selectivity. The effects of the substituents on the aromatic rings of the substrates were systematically investigated, and diverse substrates participated in the reaction with good s-values (>20) irrespective of the type of substituents and their patterns, except for o-methoxy group.

Access to optically pure β-hydroxy esters via non-enzymatic kinetic resolution by a planar-chiral DMAP catalyst

The development of new approaches to obtain optically pure β-hydroxy esters is an important area in synthetic organic chemistry since they are precursors of other high value compounds. Herein, the kinetic resolution of racemic β-hydroxy esters using a planar-chiral DMAP derivative catalyst is presented. Following this procedure, a range of aromatic β-hydroxy esters was obtained in excellent selectivities (up to s = 107) and high enantiomeric excess (up to 99% ee). Furthermore, the utility of the present method was demonstrated in the synthesis of (S)-3-hydroxy-N-methyl-3-phenylpropanamide, a key intermediate for bioactive molecules such as fluoxetine, tomoxetine or nisoxetine, in its enantiomerically pure form.

Dimethylzinc-mediated, oxidatively promoted Reformatsky reaction of ethyl iodoacetate with aldehydes and ketones

A practical and general Reformatsky reaction, promoted by oxidants and mediated by dimethylzinc, is described. The reaction is fast and runs at 0°C with aldehydes and ketones, under mild reaction conditions. Preliminary results obtained for the enantioselective version show that inexpensive chiral amino alcohols could be used in the challenging formation of enantioenriched quaternary stereogenic centers.

Catalytic enantioselective reformatsky reaction of alkyl iodoacetate with aldehydes catalyzed by chiral schiff base

The catalytic enantioselective Reformatsky reaction with aldehydes catalyzed by chiral Schiff base 1 in the presence of Me2Zn under Ar-O2 atmosphere was achieved (up to 72% ee). This process provides a potential method for the synthe