3316-42-5

Upstream product

• 51608-60-7 N-(benzylidene)-p-methylbenzenesulfonamide 
• 100-52-7 benzaldehyde 
• 530-36-9 erythro-2-amino-1,2-diphenylethanol 
• 98-59-9 p-toluenesulfonyl chloride 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 18303-04-3 N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide 
• 65996-43-2 N₁-(1-methyl-2-oxo-2-phenylethyl)-4-methyl-1-benzenesulfonamide 
• 885-75-6 2-amino-1,2-diphenyl-ethanone; hydrochloride 
• 32493-66-6 2-(2-oxo-1,2-diphenylethyl)isoindoline-1,3-dione 
• 1484-50-0 desyl bromide 
• 451-40-1 phenyl benzyl ketone 
• 588-59-0 stilbene 
• 127-65-1 chloroamine-T 
• 645-49-8 cis-stilben 

Relevant academic research and scientific papers

Alkene Syn- And Anti-Oxyamination with Malonoyl Peroxides

Malonoyl peroxide 6 is an effective reagent for the syn- or anti-oxyamination of alkenes. Reaction of 6 and an alkene in the presence of O-tert-butyl-N-tosylcarbamate (R3 = CO2 tBu) leads to the anti-oxyaminated product in up to 99% yield. Use of O-methyl-N-tosyl carbamate (R3 = CO2Me) as the nitrogen nucleophile followed by treatment of the product with trifluoroacetic acid leads to the syn-oxyaminated product in up to 77% yield. Mechanisms consistent with the observed selectivities are proposed.

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.

Pd(ii)-Catalyzed aerobic 1,2-difunctionalization of conjugated dienes: Efficient synthesis of morpholines and 2-morpholones

A novel and efficient methodology concerning the Pd(ii)-catalyzed intermolecular difunctionalization of conjugated dienes is reported to synthesize a series of functionalized morpholines and 2-morpholones. Widely distributed and easily obtained β-amino alcohols and α-amino acids, as starting nitrogen and oxygen sources, are successfully applied in the difunctionalization of conjugated dienes respectively. The majority of the desired products were obtained in moderate to excellent yields. Oxygen was successfully employed as a terminal oxidant. Further transformation of the generated products allowed for the expansion of structural diversity.

An iodine(iii) mediated oxidative rearrangement of enamines: efficient synthesis of α-amino ketones

An iodine(iii)-mediated, group-selective oxidative rearrangement of β,β-diarylenamines to α-amino ketones has been accomplished with excellent yield. The developed reaction involves the initial oxidation of enamine to an α-acyloxyimine intermediate and concomitant semipinacol rearrangement.

Cis -1,2-Aminohydroxylation of Alkenes Involving a Catalytic Cycle of Osmium(III) and Osmium(V) Centers: OsV(O)(NHTs) Active Oxidant with a Macrocyclic Tetradentate Ligand

Catalytic activity of [OsIII(OH)(H2O)(L-N4Me2)](PF6)2 (1: L-N4Me2 = N,N′-dimethyl-2,11-diaza-[3,3](2,6)pyridinophane) in 1,2-cis-aminohydroxylation of alkenes with sodium N-chloro-4-methylbenzenesulfonamide (chloramine-T) is explored. Simple alkenes as well as those containing several types of substituents are converted to the corresponding 1,2-aminoalcohols in modest to high yields. The aminoalcohol products have exclusively cis conformation with respect to the introduced -OH and -NHTs groups. The spectroscopic measurements including cold mass spectroscopic study of the reaction product of complex 1 and chloromine-T as well as density functional theory (DFT) calculations indicate that an oxido-aminato-osmium(V) species [OsV(O)(NHTs)(L-N4Me2)](PF6)2 (2) is an active oxidant for the aminohydroxylation. The DFT calculations further indicate that the reaction involves a [3 + 2] cycloaddition between 2 and alkene, and the regioselectivity in the aminohydroxylation of unsymmetrical alkenes is determined by the orientation that bears less steric hindrance from the tosylamino group, which leads to the energetically more preferred product isomer.

NaHSO3-Promoted ring openings of n-tosylaziridines and epoxides with H2O

NaHSO3-oriented ring openings of a wide variety of N-tosylaziridines and epoxides with H2O under mild conditions in acetone was found to be a convenient and effective method, which provided the desired ss-aminoalcohols and ss-diols in good to excellent yields and with uniformly high regioselectivity.

A convenient and highly productive aminohydroxylation protocol employing an osmium-diamine catalyst

In situ generated osmium-diamine chelates from 2,3-diaminopropionic acid or diaminosuccinic acid represent efficient catalysts for the highly productive aminohydroxylation of alkenes. The reaction can be employed with various osmium salts and successful c

Asymmetric synthesis of anti- and syn-β-amino alcohols by reductive cross-coupling of transition metal-coordinated planar chiral arylaldehydes with aldimines

Samarium iodide-mediated cross-coupling of N-tosyl ferrocenylideneamine with planar chiral ferrocenecarboxaldehydes or benzaldehyde chromium complexes gave diastereoselectively the corresponding anti-β-amino alcohol derivatives in good yields, while N-tosyl benzylideneamine produced syn-β-amino alcohols by coupling with planar chiral arylaldehydes. Dynamic kinetic resolution of a configurationally equilibrated reactive species generated from achiral N-tosyl ferrocenilideneamine and benzylideneamine by reduction with samarium iodide was observed in the cross-coupling with planar chiral arylaldehydes giving both antipodes of β-amino alcohols depending on the planar chirality. The obtained anti-β-amino alcohol with the ferrocene ring was utilized as a chiral ligand for catalytic asymmetric reduction of acetophenone.