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• 22651-87-2 cyclohexanecarboxylic acid anhydride 
• 1760-46-9 diphenylacetic anhydride 
• 14990-09-1 tert-butyl cinnamate 
• 108-24-7 acetic anhydride 
• 1006696-28-1 (S)-tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-phenylpropanoate 
• 49827-15-8 t-butyl iodoacetate 
• 100-52-7 benzaldehyde 
• 58059-08-8 tert-butyl (R)-p-toluenesulfinylacetate 
• 540-88-5 acetic acid tert-butyl ester 
• 54441-66-6 tert-butyl benzoylacetate 
• 51656-70-3 (2-tert-butoxy-2-oxoethyl)zinc(II) bromide 
• 63741-23-1 α-(p-tolylsulfinyl) β-hydroxy β-phenyl propionate de t-butyle 

Relevant academic research and scientific papers

Enantioselective reformatsky reaction induced by chiral β-amino alcohols

Reformatsky reagent derived from tert-butyl α-bromoacetate adds to carbonyl compounds in the presence of chiral amino alcohols leading to β-hydroxy tert-butyl eaters with good e.e. The enantioface differentiation depends on the reaction conditions and on

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.).

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)

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.

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

(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.

Paracyclophane-based carbene-copper catalyst tuned by transannular electronic effects for asymmetric boration

A series of planar chiral carbene-copper complexes based on the [2.2]paracyclophane backbone with a pseudo-ortho substitution pattern have been synthesized and applied to asymmetric β-boration of α,β-unsaturated esters. As a result, transannular electronic effects of the substituent of the chiral catalyst have significant influence on the catalytic performance. A variety of chiral β-hydroxyl esters were obtained in excellent enantioselectivities (up to 97% ee) and yields (up to 99%).

Application of bidentate oxazoline-carbene ligands with planar and central chirality in asymmetric β-Boration of α,β-unsaturated esters

A series of new oxazoline-substituted imidazolium salts based on [2.2]paracyclophane were synthesized and characterized. The new bidentate oxazoline-carbene precursor with planar and central chirality had significant advantage than the bicyclic 1,2,4-triazolium salt derived from [2.2]paracyclophane as a monodentate carbene ligand in Cu(I)-catalyzed asymmetric β-boration of α,β-unsaturated esters, giving the desired products in high enantioselectivities and yields.

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.

Asymmetric β-boration of α,β-unsaturated carbonyl compounds promoted by chiral rhodium-bisoxazolinylphenyl catalysts

Chiral rhodium-bisoxazolinylphenyl acetate complexes exhibited high catalytic activity for the β-boration of α,β-unsaturated carbonyl compounds with bis(pinacolato)diboron in the presence of sodium t-butoxide with enantioselectivity up to 97%.