97305-96-9

Upstream product

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

Downstream Products

• 72357-10-9 N-Benzyl-N-((Z)-1-phenyl-propenyl)-acetamide 
• 20306-86-9 (S)-N-(1-phenylpropyl)acetamide 
• 2698-79-5 (R)-N-(1-phenylpropyl)acetamide 
• 20306-86-9 N-(1-phenylpropyl)acetamide 
• 1225220-13-2 C₂₇H₂₇N₃O₅ 
• 1258730-24-3 diisopropyl 1-((1S,2S)-1-acetamido-1-phenylpropan-2-yl)hydrazine-1,2-dicarboxylate 

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.

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.

Transition metal complex, chiral alpha-amino tertiary borate and preparing methods thereof

The invention discloses a transition metal complex, chiral alpha-amino tertiary borate and preparing methods thereof. The chiral alpha-amino tertiary borate preparing method comprises the step of mixing a compound II, a metal ligand complex and bis(pinaco

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

Synthesis of chiral α-amino tertiary boronic esters by enantioselective hydroboration of α-arylenamides

The rhodium-catalyzed asymmetric hydroboration of α-arylenamides with BI-DIME as the chiral ligand and (Bpin)2 as the reagent yields for the first time a series of α-amino tertiary boronic esters in good yields and excellent enantioselectivities (up to 99% ee).

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.

N, N′-dioxide-Cu(OTf)2 complex catalyzed highly enantioselective amination reaction of N-acetyl enamide

The N,N′-dioxide-Cu(OTf)2 complexes were applied in the asymmetric amination reaction of N-acetyl enamides with dialkyl azodicarboxylate, giving the corresponding products in good yields with high enantioselectivities (up to 91% ee). Precursors of vicinal diamine were readily obtained with excellent diastereoselectivities (>95:5) by NaBH4 reduction.