118284-49-4

Upstream product

• 72846-70-9 isopropyl phenyl ketoxime 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 75-05-8 acetonitrile 
• 611-69-8 rac-2-methyl-1-phenylpropan-1-ol 
• 35129-66-9 2-methyl-1-phenylpropan-1-imine 
• 536-74-3 phenylacetylene 
• 611-70-1 phenyl isopropyl ketone 

Downstream Products

• 26919-86-8 (R)-(+)-N-acetyl-2-methyl-1-phenylpropylamine 
• 62474-74-2 N-((S)-2-Methyl-1-phenyl-propyl)-acetamide 
• 7476-41-7 2-methyl-1-oxo-1-phenylpropan-2-yl acetate 
• 72357-07-4 N-benzyl-N-(1-phenyl-2-methylprop-1-en-1-yl)acetamide 

Relevant academic research and scientific papers

Efficient and practical synthesis of N-acetyl enamides from ketoximes by unique iron catalytic system

A new procedure for the iron-catalyzed synthesis of enamides from ketoximes was developed, and its mechanism was proposed. A unique reduction system, with the concerted use of KI and Na2S2O4, was involved. The reaction exhibited a wide substrate scope and gave good yields in a short reaction time. The procedure is operationally simple and also applicable for the large-scale synthesis.

One-Pot Synthesis of Trisubstituted Triazenes from Grignard Reagents and Organic Azides

A simple and versatile method for the preparation of linear, trisubstituted triazenes is reported. The procedure is based on the reaction of Grignard reagents with 1-azido-4-iodobutane or 4-azidobutyl-4-methylbenzenesulfonate. These organic azides enable the regioselective formation of triazenes via an intramolecular cyclization step. The new method can be used for the preparation of aryl, heteroaryl, vinyl, and alkyl triazenes. The synthetic utility of vinyl triazenes is demonstrated by acid-induced C-N, C-O, C-F, C-P, and C-S bond-forming reactions.

Axially Chiral Enamides: Substituent Effects, Rotation Barriers, and Implications for their Cyclization Reactions

The barrier to rotation around the N-alkenyl bond of 38 N-alkenyl-N-alkylacetamide derivatives was measured (ΔG∞ rotation varied between -1). The most important factor in controlling the rate of rotation was the level of alkene substitution, followed by the size of the nitrogen substituent and, finally, the size of the acyl substituent. Tertiary enamides with four alkenyl substituents exhibited half-lives for rotation between 5.5 days and 99 years at 298 K, sufficient to isolate enantiomerically enriched atropisomers. The radical cyclizations of a subset of N-alkenyl-N-benzyl-α-haloacetamides exhibiting relatively high barriers to rotation round the N-alkenyl bond (ΔG∞ rotation >20 kcal mol-1) were studied to determine the regiochemistry of cyclization. Those with high barriers (>27 kcal mol-1) did not lead to cyclization, but those with lower values produced highly functionalized γ-lactams via a 5-endo-trig radical-polar crossover process that was terminated by reduction, an unusual cyclopropanation sequence, or trapping with H2O, depending upon the reaction conditions. Because elevated temperatures were necessary for cyclization, this precluded study of the asymmetric transfer in the reaction of individual atropisomers. However, enantiomerically enriched atropsiomeric enamides should be regarded as potential asymmetric building blocks for reactions that can be accomplished at room temperature.

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.

Synthesis of enamides via Rh/C-catalyzed direct hydroacylation of ketoximes

(Chemical Equation Presented) Enamides were efficiently prepared via a novel Rh/C-catalyzed direct hydroacylation of ketoximes. Up to 88% isolated yield of enamides were obtained with this method. Subsequent asymmetric hydrogenation of the enamides with Rh/DuanPhos complex gave the corresponding chiral amine in excellent enantioselectivities (up to 99.7% ee).