88082-67-1

Upstream product

• 88784-94-5 4-nitro-benzoic acid-((1RS,2RS)-2-hydroxy-1-phenyl-propylamide) 
• 127209-38-5 1-Dimethylsilanyl-2,2,3-trimethyl-4-phenyl-[1,2]azasiletidine 
• 90917-82-1 5-methyl-4-phenyl-4,5-dihydro-oxazol-2-ylamine 
• 622-42-4 1-nitro-1-phenylmethane 
• 75-07-0 acetaldehyde 
• 122898-35-5 C₁₆H₁₇NO₃ 
• 103-79-7 1-phenyl-acetone 
• 167083-50-3 (1S,2R)-1-azido-1-phenylpropane-2-ol 
• 25355-34-4 1-phenyl-propane-1,2-dione 1-oxime 
• 4541-87-1 cis-1-phenylpropene oxide 
• 766-90-5 cis-1-phenyl-1-propylene 
• 88784-94-5 4-nitro-benzoic acid-((1RS,2SR)-2-hydroxy-1-phenyl-propylamide) 
• 19901-87-2 threo-amino-1-phenyl-1-propanol-2 
• 122898-35-5 C₁₆H₁₇NO₃ 

Downstream Products

• 2165-67-5 (1RS,2SR)-1-amino-1-cyclohexyl-propan-2-ol 
• 88784-94-5 4-nitro-benzoic acid-((1RS,2SR)-2-hydroxy-1-phenyl-propylamide) 
• 127744-61-0 (1S,2R)-1-Phenyl-2-{[1-thiophen-2-yl-meth-(E)-ylidene]-amino}-propan-1-ol 
• 19901-87-2 (1R,2S/1R,2R)-1-amino-1-phenylpropan-2-ol 
• 88784-94-5 4-nitro-benzoic acid-((1RS,2RS)-2-hydroxy-1-phenyl-propylamide) 
• 159406-31-2 (4S,5R)-5-Methyl-4-phenyl-2-oxazolidinone 
• 526217-24-3 tert-butyl (1S,2R)-2-hydroxy-1-phenylpropylcarbamate 
• 88122-90-1 (+/-)-5c-methyl-2,4r-diphenyl-4,5-dihydro-oxazole 

Relevant academic research and scientific papers

High Regio- and Stereoselective Multi-enzymatic Synthesis of All Phenylpropanolamine Stereoisomers from β-Methylstyrene

We present a one-pot cascade for the synthesis of phenylpropanolamines (PPAs) in high optical purities (er and dr up to >99.5 %) and analytical yields (up to 95 %) by using 1-phenylpropane-1,2-diols as key intermediates. This bioamination entails the combination of an alcohol dehydrogenase (ADH), an ω-transaminase (ωTA) and an alanine dehydrogenase to create a redox-neutral network, which harnesses the exquisite and complementary regio- and stereo-selectivities of the selected ADHs and ωTAs. The requisite 1-phenylpropane-1,2-diol intermediates were obtained from trans- or cis-β-methylstyrene by combining a styrene monooxygenase with epoxide hydrolases. Furthermore, in selected cases, the envisioned cascade enabled to obtain the structural isomer (1S,2R)-1-amino-1-phenylpropan-2-ol in high optical purity (er and dr >99.5 %). This is the first report on an enzymatic method that enables to obtain all of the four possible PPA stereoisomers in great enantio- and diastereo-selectivity.

Regio- and stereoselective multi-enzymatic aminohydroxylation of β-methylstyrene using dioxygen, ammonia and formate

We report an enzymatic route for the formal regio- and stereoselective aminohydroxylation of β-methylstyrene that consumes only dioxygen, ammonia and formate; carbonate is the by-product. The biocascade entails highly selective epoxidation, hydrolysis and hydrogen-borrowing alcohol amination. Thus, β-methylstyrene was converted into 1R,2R and 1S,2R-phenylpropanolamine in 59-63% isolated yields, and up to >99.5 : 0.5 dr and er.

Examining the origin of selectivity in the reaction of racemic alcohols with chiral N-phosphoryl oxazolidinones

A range of known and novel N-phosphoryl oxazolidinones and imidazolidinones were prepared and screened in the kinetic resolution of a range of racemic magnesium chloroalkoxides. Models are proposed to account for the enantioselectivity achieved based on a combination of chiral relay effects, generation of transient stereochemistry and the structure of the intermediate magnesium alkoxide.

Enantioselective synthesis of cyclic sulfamidates by using chiral rhodium-catalyzed asymmetric transfer hydrogenation

Asymmetric transfer hydrogenation (ATH) of cyclic sulfamidate imines 4 and 9, using a HCO2H/Et3N mixture as the hydrogen source and well-defined chiral Rh catalysts (S,S)- or (R,R)-2, CpRhCl(TsDPEN), effectively produces the corresponding cyclic sulfamidates with excellent yields and enantioselectivities at room temperature within 0.5 h. ATH of 4,5-disubstituted imines 9, having preexisting stereogenic centers, is shown to take place with dynamic kinetic resolution.

Platinum-Catalyzed Intramolecular Hydrosilation of Allylamines: Formation of 1-Aza-2-silacyclobutanes and Application to Stereoselective Synthesis of 2-Amino Alcohols

N,N-Bis(dimethylsilyl)allylamines undergo intramolecular hydrosilation in the presence of Pt2O>2 (0.2 mol percent) to form four-membered cyclic compounds, 1-aza-2-silacyclobutane derivatives, which can be transformed into 2-amino alcohols by oxidation with 30percent H2O2 in the presence of KF and KHCO3.

DIASTEREOSELECTIVE PREPARATION OF ANTI-β-AMINO ALCOHOLS VIA MICHAEL ADDITION OF ALKOXIDE ANIONS TO NITROOLEFINS AND SUBSEQUENT HYDROGENATION REACTION

Diastereoselective conjugate addition of benzylalkoxide anion to nitroolefins and subsequent hydrogenation reaction provide a new convenient method for the preparation of anti-β-amino alcohols.

STEREOSELECTIVE CATALYTIC HYDROGENERATION OF alpha -HYDROXY KETOXIMES.

Two isomers (E and Z) of benzoin oxime and 2-hydroxy-1-phenyl-1-propanone oxime were catalytically hydrogenated by using palladium on charcoal and erythro amino alcohols were obtained in about 80% diastereomeric excess. The syn-anti isomerization of these oximes in the presence of palladium on charcoal was also studied in connection with the stereoselectivity of the catalytic hydrogenation of the oximes.