108591-33-9

Upstream product

• 492-41-1 (1R,2S)-norephedrine 
• 98-59-9 p-toluenesulfonyl chloride 
• 540-88-5 acetic acid tert-butyl ester 
• 594836-47-2 2-Methyl-propane-2-sulfinic acid (1R,2S)-1-phenyl-2-(toluene-4-sulfonylamino)-propyl ester 
• 64274-26-6 4-methyl-N-(1-oxo-1-phenylpropan-2-yl)benzene sulfonamide 
• 540-63-6 ethane-1,2-dithiol 
• 128227-37-2 (2S,3R)-3-Hydroxy-N-methoxy-2-methyl-3-[(2R,4R,5S)-4-methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-propionamide 
• 37577-28-9 (1S,2R)-(+)-norphedrine 
• 1369998-47-9 (1R,2R)-1-phenyl-2-(1-piperidinyl)-1-chloropropane hydrochloride 
• 40626-29-7 Acutrim 
• 40949-56-2 N-(p-toluenesulphonylimino)pyridinium ylide 
• 873-66-5 1-propenylbenzene 
• 766-90-5 cis-1-phenyl-1-propylene 
• 109-80-8 1.3-propanedithiol 

Downstream Products

• 143738-96-9 (2S,4S,5R)-2-isopropenyl-4-methyl-5-phenyl-3-(toluene-4'-sulfonyl)-oxazolidine 
• 143738-99-2 (2S,4S,5R)-2-ethenyl-4-methyl-5-phenyl-3-p-toluenesulfonyloxazolidine 
• 113323-08-3 (E)-3-[(2S,4S,5R)-4-Methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-acrylic acid methyl ester 
• 139954-95-3 Propionic acid (1R,2S)-1-phenyl-2-(toluene-4-sulfonylamino)-propyl ester 
• 212912-47-5 2RS,4S,5R-4-Methyl-3-p-methylphenylsulphonyl-2-methoxy-5-phenyl-1,3-oxazolidine 
• 128504-55-2 (S)-2-[(2S,4S,5R)-4-Methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-cyclohexanone 
• 139242-01-6 (R)-2-[(2S,4S,5R)-4-Methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-cyclohexanone 
• 211869-53-3 (4S,5R)-2-Allyl-4-methyl-5-phenyl-3-(toluene-4-sulfonyl)-[1,3,2]oxazaborolidine 
• 473554-15-3 (2R,4S,5R)-4-methyl-5-phenyl-3-(toluene-4-sulfonyl)oxathiazolidine-2-oxide 
• 139954-98-6 3-Hydroxy-3-(4-methoxy-phenyl)-2-methyl-propionic acid (1R,2S)-1-phenyl-2-(toluene-4-sulfonylamino)-propyl ester 
• 139955-01-4 (R)-3-Hydroxy-2-methyl-propionic acid (1R,2S)-1-phenyl-2-(toluene-4-sulfonylamino)-propyl ester 
• 140147-63-3 (S)-3-Hydroxy-2-methyl-propionic acid (1R,2S)-1-phenyl-2-(toluene-4-sulfonylamino)-propyl ester 
• 139954-99-7 3-Hydroxy-2-methyl-pentanoic acid (1R,2S)-1-phenyl-2-(toluene-4-sulfonylamino)-propyl ester 
• 140147-59-7 (2S,3R)-3-Hydroxy-2-methyl-pentanoic acid (1R,2S)-1-phenyl-2-(toluene-4-sulfonylamino)-propyl ester 

Relevant academic research and scientific papers

Catalytic asymmetric aziridination of enol derivatives in the presence of chiral copper complexes to give optically active α-amino ketones

A series of acyclic and cyclic enol derivatives 1 has been transformed into the corresponding α-amino-functionalized ketones 2 by means of enantioselective catalytic aziridination with chiral Cu complexes, prepared in situ from [Cu(MeCN)4]PFsu

Access to Optically Pure Benzosultams by Superelectrophilic Activation

Through superacid activation, N-(arenesulfonyl)-aminoalcohols derived from readily available ephedrines or amino acids undergo an intramolecular Friedel-Crafts reaction to afford enantiopure benzosultams bearing two adjacent stereocenters in high yields with fully controlled diastereoselectivity. Low-temperature NMR spectroscopy demonstrated the crucial role played by the conformationally restricted chiral dicationic intermediates.

Asymmetric Transfer Hydrogenation: Dynamic Kinetic Resolution of α-Amino Ketones

A series of α-amino ketones were reduced using asymmetric transfer hydrogenation (ATH) through a dynamic kinetic resolution (DKR). The protecting group was matched to the reducing agent, and following optimization, a series of substrates were investigated, giving products in high diastereoselectivity, over 99% ee in several cases and full conversion. The methodology was applied to the enantioselective synthesis of an MDM2-p53 inhibitor precursor.

Chiral-Organotin-Catalyzed Kinetic Resolution of Vicinal Amino Alcohols

A highly efficient kinetic resolution of racemic amino alcohols has been achieved for the first time with a chiral tin catalyst. A chiral organotin compound with 3,4,5-trifluorophenyl groups at the 3,3′-positions of the binaphthyl framework enabled this transformation with excellent yield and high enantioselectivity. The process tolerates aryl- and alkyl-substituted amino alcohols and a variety of other substrates, affording the corresponding products in high enantioselectivity and with s factors up to >500.

METHOD FOR PRODUCING COMPOUND HAVING 1,2-AMINO ALCOHOL SKELETON

PROBLEM TO BE SOLVED: To provide a method for producing 1,2-amino alcohols that has a high regioselectivity and is safe and efficient. SOLUTION: Provided is a method for producing 1,2-amino alcohols represented by formula 3 below by letting an electrophil

Rhodium complex with unsymmetrical vicinal diamine ligand: excellent catalyst for asymmetric transfer hydrogenation of ketones

New unsymmetrical vicinal diamine ligands with systematic variation in the regio and stereo positions in the amine and sulphonamide groups were synthesized from cheap starting material such as norephedrine. Catalytic Asymmetric Transfer Hydrogenation (ATH) of aromatic alkyl ketones has been investigated using transition metal complexes and new derivatives of monotosylated unsymmetrical vicinal diamine ligands using sodium formate as the hydrogen source, in water and methanol. Chiral secondary alcohols were obtained with excellent enantioselectivity (>95% ee) and conversion of ketones (>95%) with [Rh(Cp)Cl2]2 and ligand 4 as a catalyst. Enantioselectivity was found to be slightly higher with the use of methanol as a solvent for ATH of ketones with sodium formate as the hydrogen source compared to water as a solvent and was found to be consistent with all the ketones investigated. The reaction mixture is homogeneous in methanol unlike in water, where substrate and product are insoluble in water and form separate phase, sodium formate being soluble in water. The activity and enantioselectivity obtained for ATH of ketones using [Rh(Cp)Cl2]2 and unsymmetrical vicinal diamine ligand as catalyst was comparable with the C2 symmetric benchmark ligands like TsDPEN ((1R,2R)-N-(p-tolylsulfonyl)-1,2-diphenylethylene-diamine), and TsCYDN ((1R,2R)-N-(p-tolylsulfonyl)-1,2-cyclohexyl,diamine) under similar reaction conditions. To the best of our knowledge, this is first example of the ATH of ketones with good activity and high enantioselectivity with [Rh(Cp)Cl2]2 and unsymmetrical vicinal diamine ligands as catalyst systems.

Regiospecific Intermolecular Aminohydroxylation of Olefins by Photoredox Catalysis

A simple and regiospecific aminohydroxylation of olefins by photoredox catalysis has been developed. N-protected 1-aminopyridinium salts are the key compounds and serve as amidyl radical precursors by the action of Ir photocatalysts, fac-[Ir(ppy)3/s

Stereoselective geminal difunctionalization of vinyl arenes mediated by the bromonium ion

An anti-Markovnikov geminal oxyamination of styrenyl alkenes in an intermolecular fashion using the umpolung strategy mediated by the bromonium ion is reported. Isotope labeling studies confirm the migration of the phenyl group in the semipinacol rearrang

Remarkable enantioselective α-amination in 1-phenyl-2-(N-alkylamino)- 1-propanol

(1R,2R)-1-Phenyl-1-alkyl/arylamino-2-(N-alkylamino)propane hydrochloride salts have been synthesized with high degree of enantiomeric purity from (1S,2R)-(+)-1-phenyl-2-(N-alkylamino)-1-propanol through the corresponding chloro derivatives. This reaction sequence involves three inversions with overall inversion of configuration at C-1. Copyright

A facile, one-pot synthesis of Ephedra-based aziridines

A series of enantiomerically and diastereomerically enriched N-sulfonylaziridines have been prepared by a single-pot process from (1R,2S)- and (1S,2R)-norephedrine and (1S,2S)-pseudonorephedrine. The cyclization process involved N-sulfonylation of the Ephedra alkaloid followed by O-sulfonylation with methanesulfonyl chloride. The bis(sulfonyl)Ephedra derivatives were treated with either hydrazine or sodium hydroxide to afford the N-sulfonylaziridines.