88082-68-2Relevant academic research and scientific papers
Regio- and stereoselective multi-enzymatic aminohydroxylation of β-methylstyrene using dioxygen, ammonia and formate
Corrado, Maria L.,Knaus, Tanja,Mutti, Francesco G.
supporting information, p. 6246 - 6251 (2019/12/03)
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.
Enantioselective synthesis of cyclic sulfamidates by using chiral rhodium-catalyzed asymmetric transfer hydrogenation
Kang, Soyeong,Han, Juae,Lee, Eun Sil,Choi, Eun Bok,Lee, Hyeon-Kyu
supporting information; experimental part, p. 4184 - 4187 (2010/11/19)
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.
Synthesis of enantiopure 2-amino-1-phenyl and 2-amino-2-phenyl ethanols using enantioselective enzymatic epoxidation and regio- and diastereoselective chemical aminolysis
Sello, Guido,Orsini, Fulvia,Bernasconi, Silvana,Gennaro, Patrizia Di
, p. 372 - 376 (2007/10/03)
Several enantiopure 1,2-amino alcohols have been prepared by combining a stereoselective enzymatic epoxidation of styrenes with regio- and stereoselective chemical reactions. An interesting reactivity has been noted concerning the reaction of epoxides and NH3 under microwave activation.
Stereoselective Synthesis of 1,2-Disubstituted β-Amino Alcohols by Nucleophilic Addition to N-tert-Butanesulfinyl α-Alkoxyaldimines
Evans, Jared W.,Ellman, Jonathan A.
, p. 9948 - 9957 (2007/10/03)
N-tert-Butanesulfinyl α-alkoxyaldimines are readily prepared from protected (S)-lactals without epimerization at the α-stereocenter. Addition of ethyl and phenyl Grignard reagents, as well as the titanium enolate of methyl acetate, to the N-tert-butanesul
Additions of Enantiopure α-Sulfinyl Carbanions to (S)-N-Sulfinimines: Asymmetric Synthesis of β-Amino Sulfoxides and β-Amino Alcohols
Garcia Ruano, Jose L.,Alcudia, Ana,Del Prado, Miriam,Barros, David,Carmen Maestro,Fernandez, Inmaculada
, p. 2856 - 2862 (2007/10/03)
The addition of the lithium anions derived from (R)- and (S)-methyl and -ethyl p-tolyl sulfoxides to (S)-N-benzylidene-p-toluenesulfinamide provides an easy access route to enantiomerically pure β-(N-sulfinyl)amino sulfoxides. Stereoselectivity can be ach
Platinum-Catalyzed Intramolecular Hydrosilation of Allylamines: Formation of 1-Aza-2-silacyclobutanes and Application to Stereoselective Synthesis of 2-Amino Alcohols
Tamao, Kohei,Nakagawa, Yoshiki,Ito, Yoshihiko
, p. 3438 - 3439 (2007/10/02)
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
Kamimura, Akio,Ono, Noboru
, p. 731 - 734 (2007/10/02)
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.
Harada,Shiono
, p. 1040 - 1045 (2007/10/02)
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.
Ueber die Stereoselektivitaet der 9,9'-Spirobifluoren-kronenaether gegenueber α-Aminoalkoholen
Prelog, Vladimir,Mutak, Stjepan
, p. 2274 - 2278 (2007/10/02)
Crown ethers I-VI were tested by partition experiments for their stereoselectivity towards α-amino alcohols 1-10.The stereoselectivity depends in a regular way on both the absolute and relative configuration of the crown ether and α-amino alcohol.Comments are made on some high stereoselectivities.
Ueber die Enantiomerentrennung durch Verteilung zwischen fluessigen Phasen 3. Mitteilung. Selektivitaet der lipophilen Weinsaeureester fuer chirale Ammonium-Salze verschiedener Konstitution und Konfiguration
Prelog, Vladimir,Mutak, Stjepan,Kovacevic, Krunoslav
, p. 2279 - 2284 (2007/10/02)
Several methods are described which allow determination on a small scale of the enantiomer distribution constant Q, and the affinity coefficient P, which characterize the enantioselectivity and the affinity of a lipophilic phase for ammonium salts of different constitution and configuration.The influence of concentration of the tartaric acid ester, temperature, concentration and type of the lipophilic anion on Q and P was investigated to find out favourable experimental conditions for resolutions of racemates by iterative processes, e.g. partition chromatography.The relation ship between Q and the configuration of aminoalcohols 1-12 was explored and the observed regularities are pointed out.In addition it was found that lipophilic tartaric acid esters are enantioselective to salts of threo-1,2-diphenyl-1,2-ethanediamine 13, and to phenylglycine and its derivatives 14-16.
