6966-30-9

Upstream product

• 108-24-7 acetic anhydride 
• 60-35-5 acetamide 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 60317-41-1 ethyl 2-(hydroxyimino)-3-oxo-3-phenylpropanoate 
• 98-86-2 acetophenone 
• 5453-57-6 ethyl α-phenylazobenzoylacetate 
• 75-36-5 acetyl chloride 

Downstream Products

• 3509-75-9 (1RS,2SR)-1,3-diacetoxy-2-acetylamino-1-phenyl-propane 
• 1846-33-9 N-phenacylacetamide 
• 6966-29-6 N-Acetyl-3-phenyl-serin-ethylester 
• 88854-18-6 (2S,3R)-ethyl 2-acetamido-3-acetoxy-3-phenylpropanoate 

Relevant academic research and scientific papers

Interweaving Visible-Light and Iron Catalysis for Nitrene Formation and Transformation with Dioxazolones

Herein, visible-light-driven iron-catalyzed nitrene transfer reactions with dioxazolones for intermolecular C(sp3)-N, N=S, and N=P bond formation are described. These reactions occur with exogenous-ligand-free process and feature satisfactory to excellent yields (up to 99 %), an ample substrate scope (109 examples) under mild reaction conditions. In contrast to intramolecular C?H amidations strategies, an intermolecular regioselective C?H amidation via visible-light-induced nitrene transfer reactions is devised. Mechanistic studies indicate that the reaction proceeds via a radical pathway. Computational studies show that the decarboxylation of dioxazolone depends on the conversion of ground sextet state dioxazolone-bounding iron species to quartet spin state via visible-light irradiation.

Direct Access to 1,1-Dicarbonyl Sulfoxonium Ylides from Aryl Halides or Triflates: Palladium-Catalyzed Carbonylation

The synthesis of 1,1-dicarbonyl sulfoxonium ylides by palladium-catalyzed carbonylation of aryl halides or triflates with α-carbonyl sulfoxonium ylides has been developed for the first time. This method provides a general approach to synthetically useful 1,1-dicarbonyl sulfoxonium ylides in high efficiency. The protocol displays a wide substrate scope, showing that the resulting 1,1-dicarbonyl sulfoxonium ylides have been converted into the corresponding 1,3-dicarbonyl compounds.

Highly Diastereo- and Enantioselective Access to syn-α-Amido β-Hydroxy Esters via Ruthenium-Catalyzed Dynamic Kinetic Resolution-Asymmetric Hydrogenation

Dynamic kinetic resolution (DKR) of racemic aryl α-amino β-ketoesters via Ru-diphosphine-catalyzed asymmetric hydrogenation was realized at 70 °C under 50 atm of hydrogen, affording syn α-amido β-hydroxy esters in high yields (up to 96%) with high reactivity (TON up to 940) and diastereo- and enantioselectivities (up to 99:1 dr, 98% ee). These hydrogenation products provide valuable chiral synthons in many natural products and pharmaceuticals. Gram-scale DKR asymmetric hydrogenation (DKR-AH) was also performed with retained reactivity and stereoselectivity, revealing the synthetic utility of this method.

Rhodium-catalyzed asymmetric hydrogenation of tetrasubstituted β-acetoxy-α-enamido esters and efficient synthesis of droxidopa

A rhodium-catalyzed asymmetric hydrogenation of challenging tetrasubstituted β-acetoxy-α-enamido esters was developed, giving chiral β-acetoxy-α-amido esters in high yields with excellent enantioselectivities (up to >99% ee). The products could be easily transformed to β-hydroxy-α-amino acid derivatives which are valuable chiral building blocks and a novel route for the synthesis of droxidopa was also developed.

Copper(II) triflate catalyzed amination of 1,3-dicarbonyl compounds

A method to prepare α,α-acyl amino acid derivatives efficiently by Cu(OTf)2+1,10-phenanthroline (1,10-phen)-catalyzed amination of 1,3-dicarbonyl compounds with PhI=NSO2Ar is described. The mechanism is thought to initially involve aziridination of the enolic form of the substrate, formed in situ through coordination to the Lewis acidic metal catalyst, by the putative copper-nitrene/imido species generated from the reaction of the metal catalyst with the iminoiodane source. Subsequent ring opening of the resultant aziridinol adduct under the Lewis acidic conditions then provided the α-aminated product. The utility of this method was exemplified by the enantioselective synthesis of a precursor of 3-styryl-2-benzoyl-L-alanine. Copyright

Kasumigamide, an antialgal peptide from the cyanobacterium Microcystis aeruginosa

Kasumigamide (1), a novel antialgal tetrapeptide containing an N-terminal α-hydroxy acid, was isolated from the freshwater cyanobacterium Microcystis aeruginosa (NIES-87). Its structure was elucidated by two-dimensional 1H-1H and 1H-13C NMR correlation experiments and confirmed by mass spectral and amino acid analyses. The absolute stereochemistry of 1 was determined by chemical studies. This peptide showed an antialgal activity against the green alga Chlamydomonas neglecta (NIES-439).

Reduction of Arylcarbonyl Using Zinc Dust in Acetic Acid

Zinc dust in acetic acid has been found to be a versatile and chemoselective reagent for the reduction of various arylcarbonyls to the corresponding alcohols or their acetates in fair yields.

Process for the preparation of alpha-aminoketone salts

There is disclosed a process for the preparation of an alpha-aminoketone salt of formula I STR1 which comprises reacting a nitrosated keto ester of formula II STR2 with a carboxylic anhydride of formula IV STR3 under the conditions of catalytic hydrogenation, to a compound of formula III STR4 which compound of formula III is then hydrolysed with an acid Hn A to the salt I, in which formulae above R1 is C1 -C6 alkyl, phenoxy-C1 -C4 alkyl, phenyl, C7 -C9 phenylalkyl, or phenyl or C7 -C9 phenylalkyl which are substituted by halogen, C1 -C6 alkyl or C1 -C6 alkoxy, hydroxy or cyano, R2 is C1 -C4 alkyl or cyclohexyl, n is 1 to 3, R3 is C1 -C4 alkyl and A is the radical of an organic or mineral protic acid. Pyrroles suitable as co-stabilisers for PVC can be prepared from alpha-aminoketone salts of formula I.