67341-08-6

Upstream product

• 100-42-5 styrene 
• 91174-01-5 sodium [(benzyloxy)carbonyl]chloroamide 
• 1499-00-9 2-phenylaziridine 
• 64420-86-6 O-p-toluenesulfonyl benzyloxyhydroxamate 
• 556-82-1 3-methyl-2-buten-1-ol 
• 95-13-6 1-indene 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 3426-71-9 Benzyl N-hydroxycarbamate 
• 1262306-22-8 benzyloxycarbonylamino-4-chlorobenzoate 
• 54043-04-8 (N-(Benzyloxycarbonyl)amino)-methyl phenyl ketone 
• 96-09-3 styrene oxide 
• 501-53-1 benzyl chloroformate 
• 7568-93-6 2-Amino-1-phenylethanol 
• 100-52-7 benzaldehyde 

Downstream Products

• 144315-91-3 Butyric acid (R)-2-benzyloxycarbonylamino-1-phenyl-ethyl ester 
• 144315-91-3 Butyric acid (S)-2-benzyloxycarbonylamino-1-phenyl-ethyl ester 
• 144372-50-9 (R)-benzyl N-(2-hydroxy-2-phenylethyl)carbamate 
• 500763-83-7 (S)-(+)-(2-hydroxy-2-phenyl-ethyl)-carbamic acid benzyl ester 
• 2549-14-6 (R)-2-Amino-1-phenylethanol 
• 56613-81-1 (S)-2-Amino-1-phenyl-1-ethanol 
• 4430-27-7 2-amino-1-phenylethane-1-sulfonic acid 
• 678166-60-4 2-(benzyloxycarbonyl)amino-1-phenylethyl thioacetate 

Relevant academic research and scientific papers

Novel triazole-based ligands and their zinc(II) and nickel(II) complexes with a nitrogen donor environment as potential structural models for mononuclear active sites

Three new 1,2,3-triazole-based ligands with an N,N,N coordination core were prepared using a convergent synthetic protocol starting from racemic 2-amino-1-phenylethanol. They were tested as chelators for biorelevant ZnII or NiII ions. An N,N,N ligand with a terminal amino functionality coordinated the ZnII in a bidentate fashion, not including the triazole nitrogen. The ligand with two pendant 2-pyridyl groups acted as a tridentate ligand without an N2-triazole coordination to ZnII, while the ligand containing one 2-pyridyl group acted as an inverse-click chelator for NiII ions.

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.

Direct catalytic synthesis of unprotected 2-amino-1-phenylethanols from alkenes by using iron(II) phthalocyanine

Aryl-substituted amino alcohols are privileged scaffolds in medicinal chemistry and natural products. Herein, we report that an exceptionally simple and inexpensive FeII complex efficiently catalyzes the direct transformation of simple alkenes into unprotected amino alcohols in good yield and perfect regioselectivity. This new catalytic method was applied in the expedient synthesis of bioactive molecules and could be extended to aminoetherification.

Kinetic resolution of racemic amino alcohols through intermolecular acetalization catalyzed by a chiral Bronsted acid

The kinetic resolution of racemic secondary alcohols is a fundamental method for obtaining enantiomerically enriched alcohols. Compared to esterification, which is a well-established method for this purpose, kinetic resolution through enantioselective intermolecular acetalization has not been reported to date despite the fact that the formation of acetals is widely adopted to protect hydroxy groups. By taking advantage of the thermodynamics of acetalization by the addition of alcohols to enol ethers, a highly efficient kinetic resolution of racemic amino alcohols was achieved for the first time and in a practical manner using a chiral phosphoric acid catalyst.

Osmium-catalyzed vicinal oxyamination of alkenes by N-(4- toluenesulfonyloxy)carbamates

N-(4-Toluenesulfonyloxy)carbamates based on a range of common amine protecting groups serve as preformed nitrogen sources in the intermolecular osmium-catalyzed oxyamination reaction of a variety of mono-, di-, and trisubstituted alkenes. The reactions occur with low catalyst loadings and good yields and afford high regioselectivity for unsymmetrically substituted alkenes.

IMPROVED AMINOHYDROXYLATION OF ALKENES

The invention relates to a process for the aminohydroxylation of alkenes using N-oxycarbamate reagents, e.g. N-acyloxycarbamate, N-alkyloxycarbonyloxycarbamate and N-aralkoxycarbonyloxycarbamate reagents. The invention particularly relates to an intermolecular aminohydroxylation reaction that can be carried out in the absence of added base. The invention also relates to novel N-oxycarbamate reagents that are stable crystalline materials. The process of the invention is useful in the synthesis of compounds having a vicinal amino alcohol moiety, such as biologically active compounds.

Alkyl 4-chlorobenzoyloxycarbamates as highly effective nitrogen source reagents for the base-free, intermolecular aminohydroxylation reaction

Ethyl-(7), benzyl-(8), tert-butyl-(9), and fluorenylmethyl-4- chlorobenzoyloxycarbamates (10) have been prepared as storable and easy-to-prepare nitrogen sources for use in the intermolecular Sharpless aminohydroxylation reaction and its asymmetric variant. These reagents were found to be effective under base-free reaction conditions. The scope and limitations of these methods have been explored using a variety of alkenes, among which, trans-cinnamates, in particular, proved to be good substrates.

Organic metal compound and process for preparing optically-active alcohols using the same

The present invention provides an asymmetric reduction catalyst effective in preparing optically-active alcohol compounds having various functional groups, and a process for preparing optically-active alcohol compounds using said asymmetric reduction catalyst. The organic metal compound of the present invention is represented by the following general formula (1): wherein R1 and R2 may be mutually identical or different, and are an alkyl group, a phenyl group, a naphthyl group, a cycloalkyl group, or an alicyclic ring formed by binding R1 and R2, which may have a substituent; R3 is a hydrogen atom or an alkyl group; Cp is a cyclopentadienyl group, which may have a substituent, bound to M1 via a π bond; X1 is a halogen atom or a hydrido group; M1 is rhodium or iridium; and * denotes asymmetric carbon.

A General Route to the Synthesis of N-Protected 1-Substituted and 1,2-Disubstituted Taurines

N-Benzyloxycarbonyl protected α-substituted and αβ- disubstituted taurines were synthesized from olefins and epoxides via N-benzyloxycarbonylamino alcohol thioacetates as key intermediates. They are important sulfur analogues of naturally occurring amino acids and building blocks for the synthesis of α-substituted and α,β- disubstituted β-sulfonopeptides.