97305-97-0

Upstream product

• 2157-50-8 propiophenone oxime 
• 108-24-7 acetic anhydride 
• 536-74-3 phenylacetylene 
• 29076-84-4 propiophenone-imine 
• 93-54-9 1-Phenyl-1-propanol 
• 673-32-5 1-Phenylprop-1-yne 
• 60-35-5 acetamide 
• 93-55-0 1-phenyl-propan-1-one 
• 4896-15-5 2-acetylamino-2-phenyl-butyric acid 

Downstream Products

• 876345-31-2 2-chloro-5-methyl-6-phenylnicotinaldehyde 
• 1258729-72-4 C₁₉H₂₇N₃O₅ 
• 1258730-24-3 diisopropyl 1-((1S,2S)-1-acetamido-1-phenylpropan-2-yl)hydrazine-1,2-dicarboxylate 
• 72357-09-6 (E)-N-benzyl-N-(1-phenylprop-1-en-1-yl)acetamide 
• 20306-86-9 N-(1-phenylpropyl)acetamide 
• 2698-79-5 (R)-N-(1-phenylpropyl)acetamide 

Relevant academic research and scientific papers

Combined Theoretical and Experimental Studies Unravel Multiple Pathways to Convergent Asymmetric Hydrogenation of Enamides

We present a highly efficient convergent asymmetric hydrogenation of E/Z mixtures of enamides catalyzed by N,P-iridium complexes supported by mechanistic studies. It was found that reduction of the olefinic isomers (E and Z geometries) produces chiral amides with the same absolute configuration (enantioconvergent hydrogenation). This allowed the hydrogenation of a wide range of E/Z mixtures of trisubstituted enamides with excellent enantioselectivity (up to 99% ee). A detailed mechanistic study using deuterium labeling and kinetic experiments revealed two different pathways for the observed enantioconvergence. For α-aryl enamides, fast isomerization of the double bond takes place, and the overall process results in kinetic resolution of the two isomers. For α-alkyl enamides, no double bond isomerization is detected, and competition experiments suggested that substrate chelation is responsible for the enantioconvergent stereochemical outcome. DFT calculations were performed to predict the correct absolute configuration of the products and strengthen the proposed mechanism of the iridium-catalyzed isomerization pathway.

Merging NiH Catalysis and Inner-Sphere Metal-Nitrenoid Transfer for Hydroamidation of Alkynes

The formal hydroamination/hydroamidation utilizing metal hydride is an appealing synthetic tool for the construction of valuable nitrogen-containing compounds from unsaturated hydrocarbons. While significant advances have been made for the functionalizations of alkenes in this realm, the direct hydroamidation of alkynes remains rather limited due to the high feasibility of the key metal-alkenyl intermediate to choose other reaction pathways. Herein, we report a NiH-catalyzed strategy for the hydroamidation of alkynes with dioxazolones, which allows convenient access to synthetically useful secondary enamides in (E)-anti-Markovnikov or Markovnikov selectivity. The reaction is viable for both terminal and internal alkynes and is also tolerant with a range of subtle functional groups. With H2O found as an essential component for high catalyst turnovers, the involvement of inner-sphere nitrenoid transfer is proposed that outcompetes an undesired semireduction process, thus representing the first example to show the competence of Ni catalysis for metal-nitrenoid formation from dioxazolones.

Synthesis of Functionalized Vinylsilanes via Metal-Free Dehydrogenative Silylation of Enamides

A novel method of metal-free dehydrogenative silylation of enamides has been developed. The desired functionalized vinylsilane products were obtained in moderate to good yield and with high stereoselectivities. This protocol displays good tolerance of various functionalities. Furthermore, the high chemoselectivity of this reaction enables us to introduce different unsaturated C-C moieties to the products. The ease of further derivatization of the products to other useful compounds also demonstrates the highly synthetic utility of the current methodology.

Photoredox/Cobalt Dual-Catalyzed Decarboxylative Elimination of Carboxylic Acids: Development and Mechanistic Insight

Recently, dual-catalytic strategies towards the decarboxylative elimination of carboxylic acids have gained attention. Our lab previously reported a photoredox/cobaloxime dual catalytic method that allows the synthesis of enamides and enecarbamates directly from N-acyl amino acids and avoids the use of any stoichiometric reagents. Further development, detailed herein, has improved upon this transformation's utility and further experimentation has provided new insights into the reaction mechanism. These new developments and insights are anticipated to aid in the expansion of photoredox/cobalt dual-catalytic systems.

Decarboxylative Elimination of N-Acyl Amino Acids via Photoredox/Cobalt Dual Catalysis

A dual-catalytic strategy for the synthesis of enamides and enecarbamates directly from easily accessible and inexpensive amino acids has been realized. This mild and efficient protocol makes use of an organic photoredox catalyst and a cobaloxime catalyst to achieve decarboxylative elimination using hydrogen evolution to drive the oxidation. Thus, the reaction occurs without a stoichiometric oxidant or the forcing conditions previously employed in attempts to achieve similar eliminations.

CATALYTIC PREPARATION OF ENAMIDES FROM ALKYL AZIDES AND ACYL DONORS

The present invention relates to a method to synthesize an enamide compound by generating imine which does not have a substituent group bonded to the nitrogen from an organic azide compound and conducting a reaction of the same with acyl doner. By using t

One-pot green synthesis of enamides and 1,3-diynes

A green organic synthetic method combining reductive acylation of ketoximes and oxidative coupling of terminal alkynes was developed. This novel process enables enamides and 1,3-diynes to be synthesized simultaneously in high yields and under mild conditions without the use of terminal reductants/oxidants.

Exploiting the Nucleophilicity of N-H Imines: Synthesis of Enamides from Alkyl Azides and Acid Anhydrides

The nucleophilicity of N-unsubstituted imines, which were generated from alkyl azides by a ruthenium-catalyzed reaction, was investigated in the reaction with acid anhydrides. The initial products were N-acylimines, which isomerized to the corresponding e

An efficient preparation of N-acetyl enamides catalyzed by Ru(II) complexes

Reductive acetylation of ketoximes to give the corresponding acyl enamides can be achieved by using 1-3 mol % of [RuCl2(p-cymene)]2 as the catalyst in the presence of KI as the reducing agent in high yields. This procedure has been applied to synthesize N-[1-(1,3-benzodioxol-5-yl)-1-butenyl] acetamide (6), which is the intermediate for the synthesis of DMP 777, an inhibitor of leukocyte elastase.

Synthesis of enamides via CuI-catalyzed reductive acylation of ketoximes with NaHSO33

CuI-catalyzed reductive acylation of ketoximes for preparation of enamides was reported. A broad scope of enamides was obtained in high yields with NaHSO3 used as the terminal reductant.