300345-91-9

Upstream product

• 1085390-48-2 N-((1S,2R)-2-azido-1,2-diphenylethyl)benzenesulfonamide 
• 1085390-46-0 N-((1R,2S)-2-azido-1,2-diphenylethyl)benzenesulfonamide 
• 1085390-52-8 N-((1S,2S)-2-azido-1,2-diphenylethyl)benzenesulfonamide 
• 1085390-50-6 N-((1R,2R)-2-azido-1,2-diphenylethyl)benzenesulfonamide 
• 29841-69-8 (S,S)-1,2-diphenyl-1,2-diaminoethane 
• 98-09-9 benzenesulfonyl chloride 
• 35132-20-8 (R,R)-1,2-diphenylethylenediamine 

Relevant academic research and scientific papers

Enantioselective Hydroboration of Ketones Catalyzed by Rare-Earth-Metal Complexes Supported with Phenoxy-Functionalized TsDPEN Ligands

Six novel chiral rare-earth-metal complexes bearing the phenoxy-functionalized TsDPEN ligand H3L1 (H3L1 = N-((1R,2R)-2-((3,5-di-Tert-butyl-2-hydroxybenzyl)amino)-1,2-diphenylethyl)-4-methylbenzenesulfonamide) were synthesized successfully and well characterized. The solid-state structures of four tetranuclear rare-earth-metal complexes [RE2L13]2 (RE = Nd (1), Sm (2), Eu (3), Gd (4)) and the dual-core yttrium complex Y2L13 (5) were determined by X-ray diffraction, respectively. The structure of lanthanum complex 6 was speculated by the 1H DOSY spectroscopy in THF-d8 together with DFT calculations. Complexes 1-5 were employed to catalyze the enantioselective hydroboration of ketones and α,β-unsaturated ketones using pinacolborane (HBpin) as a reductant, and complex 1 gave better outcomes in comparison to the others. The corresponding secondary alcohols were obtained in excellent yields and moderate ee values. The same results were also achieved using the combined catalyst system of the neodymium amide Nd[N(SiMe3)2]3 with the phenoxy-functionalized TsDPEN ligand H3L1 in a 1:1.5 molar ratio.

A four-hydrogenated 1, 8 - naphthyridine apperception composition preparation method and its prepared chiral products

The invention discloses a preparation method of a tetrahydro 1, 8-naphthyridine compound. The preparation method comprises the following steps: under the existence of a chiral catalyst, enabling a compound with the structure shown in the formula (1) (in the description) and hydrogen to be subjected to addition reaction, wherein the chiral catalyst is a coordination compound with the structure shown in the formula (2) (in the description). The invention further provides a chiral product of the tetrahydro 1, 8-naphthyridine compound, prepared through the preparation method. According to the invention, the proper compound with the structure shown in the formula (1) (in the description) is used as a substrate, and the proper coordination compound with the structure shown in the formula (2) (in the description) is used as the chiral catalyst to perform selective hydrogenation reduction on 1, 8-naphthyridine compound with the structure shown in the formula (1) by adopting hydrogen, so that the chiral product of the tetrahydro 1, 8-naphthyridine compound is prepared with low cost. The chiral product of the tetrahydro 1, 8-naphthyridine compound can be used as a biologically active compound and a structural building block of a chiral drug.

O-bicyclic amine compounds as well as preparation method and chiral products thereof

The invention relates to the field of asymmetric synthesis methods, and discloses a preparation method of o-bicyclic amine compounds. The method comprises the step of enabling a compound having a structure as shown in a formula (1) and hydrogen to be subjected to an addition reaction in presence of a chiral catalyst, wherein the chiral catalyst is a complex having a structure as shown in a formula (2). The invention also provides chiral products of the o-bicyclic amine compounds prepared by the method, and the o-bicyclic amine compounds. After the method is adopted, the selective hydrogenation reduction of the compound having the structure as shown in the formula (1) is realized by using the hydrogen, so that octahydrogenated products, i.e., the o-bicyclic amine compounds shown in a formula (4) are produced with low cost. The formula (1), the formula (2) and the formula (4) are described in the description.

A four-hydrogenated 1, 5 - naphthyridine apperception composition preparation method and its prepared chiral products

The invention discloses a method for preparing a tetrahydro-1,5-naphthyridine compound. The method comprises the following steps: carrying out an addition reaction between a compound with the structure shown as a formula (1) and hydrogen in the presence of a chiral catalyst, wherein the chiral catalyst is a coordination complex with a structure shown as a formula (2). The invention also provides a chiral product of the tetrahydro-1,5-naphthyridine compound prepared by the method. The proper compound with the structure shown as the formula (1) is selected as a substrate, the proper coordination complex with the structure shown as the formula (2) is selected as the chiral catalyst, and selective hydrogenation reduction of the 1,5-naphthyridine compound with the structure shown as the formula (1) is realized by adopting hydrogen, so that the chiral product of the tetrahydro-1,5-naphthyridine compound is prepared at low cost. The chiral product of the tetrahydro-1,5-naphthyridine compound prepared by the invention can serve as a structure block of bioactive compounds and chiral drugs.

Ir(III) complexes of diamine ligands for asymmetric ketone hydrogenation

The use of a combination of IrCl3 with a series of ligands derived from the C2-symmetric diamine diphenylethanediamine (DPEN) forms a catalyst capable of the asymmetric hydrogenation of ketones in up to 85% ee.

Synthesis of chiral organocatalysts derived from aziridines: Application in asymmetric aldol reaction

(Chemical Equation Presented) We report the synthesis of a new series of highly efficient chiral organocatalysts derived via the regio-and stereoselective ring opening of chiral aziridines with azide anions. The catalysts have proved to be very efficient

Biomimetic iron-catalyzed asymmetric epoxidation of aromatic alkenes by using hydrogen peroxide

A novel and general biomimetic non-heme Fe-catalyzed asymmetric epoxidation of aromatic alkenes by using hydrogen peroxide is reported herein. The catalyst consists of ferric chloride hexahydrate (FeCl3·OH 2O), pyridine-2,6-dicarboxylic acid (H2-(pydic)), and readily accessible chiral N-arenesulfonyl-N′-benzyl-substituted ethylenediamine ligands. The asymmetric epoxidation of styrenes with this system gave high conversions but poor enantiomeric excesses (ee), whereas larger alkenes gave high conversions and ee values. For the epoxidation of trans-stilbene (1a), the ligands (S,S)-N-(4-toluenesulfonyl)-1,2- diphenylethylenediamine ((S,S)-4a) and its N′-benzylated derivative ((S,S)-5a) gave opposite enantiomers of trans-stilbene oxide, that is, (S,S)-2a and (R,R)-2a, respectively. The enantioselectivity of alkene epoxidation is controlled by steric and electronic factors, although steric effects are more dominant. Preliminary mechanistic studies suggest the in situ formation of several chiral Fe-complexes, such as [FeCl(L*)2-(pydic)] ·HCl (L* = (S,S)-4a or (S,S)-5a in the catalyst mixture), which were identified by ESIMS. A UV/Vis study of the catalyst mixture, which consisted of FeCl3·6H2O, H2(pydic), and (S,S)-4a, suggested the formation of a new species with an absorbance peak at λ = 465 nm upon treatment with hydrogen peroxide. With the aid of two independent spin traps, we could confirm by EPR spectroscopy that the reaction proceeds via radical intermediates. Kinetic studies with deuterated styrenes showed inverse secondary kinetic isotope effects, with values of k H/kD = 0.93 for the β carbon and kH/k D=0.97 for the a carbon, which suggested an unsymmetrical transition state with stepwise O transfer. Competitive epoxidation of para-substituted styrenes revealed a linear dual-parameter Hammett plot with a slope of 1.00. Under standard conditions, epoxidation of la in the presence of ten equivalents of H218O resulted in an absence of the isotopic label in (S,S)-2a. A positive non-linear effect was observed during the epoxidation of la in the presence of (S,S)-5a and (R,R)-5a.

Preparation of mono-N-sulphonylated diamines

The present invention relates to a process for preparing mono-N-sulphonylated diamines by reacting diamines with sulphonyl halides in the presence of water, base and organic solvents.

Process for preparing mono-N-sulfonylated diamines

Production of mono-N-sulfonylated diamine compounds comprises reaction of a diamine compound with a sulfonyl halide in the presence of water, organic solvent and a base. Production of mono-N-sulfonylated diamine compounds (I) of formula (1) comprises reaction of a diamine compound of formula (2) with a sulfonyl halide of formula (3) in the presence of water, organic solvent and a base. R3SO2X (3) R1 and R2 = 1-20C alkyl, 4-15C aryl, 5-16C arylalkyl or R1 and R2 together form a 3-12C alkylene; R3 = 1-20C alkyl, optionally fluorinated or 4-15C aryl; and X = F, Cl, Br or I. Independent claims are also included for the following: (1) solutions (II) containing the mono-N-sulfonylated diamine compounds (I) prepared by the process followed by at least partial removal of water; and (2) catalysts (III) prepared from the solutions (II) by reaction with organometallic compounds of formula (4). (MXn(R4))2 (4) M = Ru, Rh or Ir; R4 = 6-12C aryl, optionally substituted by 1-8C alkyl, benzyl or phenyl, or cyclopentadienyl optionally substituted by up to 5 groups or indenyl; and n = 1 or 2.

METHOD FOR THE PREPARATION OF TRICYCLIC AMINO ALCOHOL DERIVATIVES THROUGH AZIDES

The present invention is directed to processes for the preparation of a tricyclic amino-alcohol derivative useful for treating and preventing diabetes, obesity, hyperlipidemia and the like, which compound is represented by the formula (1): wherein R1 represents a lower alkyl group or a benzyl group; *1 represents an asymmetric carbon atom; R2 represents a hydrogen atom, a halogen atom or a hydroxyl group; and A represents one of the following groups: wherein X represents NH, O or S; R5 represents a hydrogen atom, a hydroxyl group, an amino group or an acetylamino group; and *2 represents an asymmetric carbon atom when R5 is not a hydrogen atom. The processes of the present invention proceed via azide derivatives and are convenient, practical preparing processes with low cost which comprise a small number of steps with good industrial work efficiency.