208335-82-4

Upstream product

• 123-75-1 pyrrolidine 
• 7299-58-3 phenylpropiolyl chloride 
• 637-44-5 phenylpropyolic acid 
• 120-94-5 1-Methylpyrrolidine 
• 201230-82-2 carbon monoxide 
• 536-74-3 phenylacetylene 
• 591-50-4 iodobenzene 

Downstream Products

• 1174523-69-3 (R)-8a-(but-3-enyl)-5-phenyl-6-(pyrrolidine-1-carbonyl)-2,3,8,8a-tetrahydroindolizin-7(1H)-one 
• 389572-81-0 1-{[(2S,3R)-3-phenylaziridin-2-yl]carbonyl}pyrrolidine 
• 240805-44-1 (Z)-1-(1-oxo-3-phenyl-2-propenyl)pyrrolidine 

Relevant academic research and scientific papers

Palladium(II)-Catalysed Aminocarbonylation of Terminal Alkynes for the Synthesis of 2-Ynamides: Addressing the Challenges of Solvents and Gas Mixtures

2-Ynamides can be synthesised through PdIIcatalysed oxidative carbonylation, utilising low catalyst loadings. A variety of alkynes and amines can be used to afford 2-ynamides in high yields, whilst overcoming the drawbacks associated with previ

Allenone-Mediated Racemization/Epimerization-Free Peptide Bond Formation and Its Application in Peptide Synthesis

Allenone has been identified as a highly effective peptide coupling reagent for the first time. The peptide bond was formed with an α-carbonyl vinyl ester as the key intermediate, the formation and subsequent aminolysis of which proceed spontaneously in a racemization-/epimerization-free manner. The allenone coupling reagent not only is effective for the synthesis of simple amides and dipeptides but is also amenable to peptide fragment condensation and solid-phase peptide synthesis (SPPS). The robustness of the allenone-mediated peptide bond formation was showcased incisively by the synthesis of carfilzomib, which involved a rare racemization-/epimerization-free N to C peptide elongation strategy. Furthermore, the successful synthesis of the model difficult peptide ACP (65-74) on a solid support suggested that this method was compatible with SPPS. This method combines the advantages of conventional active esters and coupling reagents, while overcoming the disadvantages of both strategies. Thus, this allenone-mediated peptide bond formation strategy represents a disruptive innovation in peptide synthesis.

Mild and efficient preparation method of alpha-acyloxy alkenyl amide compound and application thereof to synthesis of amide and polypeptide

The invention discloses a mild and efficient preparation method of an alpha-acyloxy alkenyl amide compound and application thereof to synthesis of an amide and a polypeptide. The alpha-acyloxy alkenyl amide compound is obtained by an addition reaction of alkyne amide and carboxylic acid in dichloromethane under a condition that the temperature is 0 to 50 DEG C; the product alpha-acyloxy alkenyl amide compound can generate the amide or the polypeptide with amides through combination reaction; the two reactions can be carried out step by step and can also be carried out in one pot; when the two reactions are carried out in one pot, the product alpha-acyloxy alkenyl amide compound does not need to be purified from the former reaction and the amide compound is directly added to react, wherein in the reaction of generating the amide or the polypeptide, a solvent can also be water, so that a novel method for fixed-site decoration and marking of biological macromolecules including proteins, nucleic acid and the like in a water phase is provided. The mild and efficient preparation method has moderate reaction conditions and does not need a metal catalyst; when the carboxylic acid, which has chirality on an alpha site of carboxyl, forms an amide bond or a peptide bond, no racemization occurs; the mild and efficient preparation method is simple to operate and wide in application range.

Ynamides as Racemization-Free Coupling Reagents for Amide and Peptide Synthesis

A highly efficient, two-step, one-pot synthetic strategy for amides and peptides was developed by employing ynamides as novel coupling reagents under extremely mild reaction conditions. The ynamides not only are effective for simple amide and dipeptide synthesis but can also be used for peptide segment condensation. Importantly, no racemization was detected during the activation of chiral carboxylic acids. Excellent amidation selectivity toward amino groups in the presence of -OH, -SH, -CONH2, ArNH2, and the NH of indole was observed, making the protection of these functional groups unnecessary in amide and peptide synthesis.

Palladium-Catalyzed Oxidative N-Dealkylation/Carbonylation of Tertiary Amines with Alkynes to α,β-Alkynylamides

The first highly effective Pd/C-catalyzed oxidative N-dealkylation/carbonylation of various aliphatic as well as cyclic tertiary amines with alkynes has been described. The selective sp3 C-N bond activation of tertiary amines at the less steric side using O2 as a sole oxidant and a plausible reaction pathway for the reaction are discussed. The general and operationally simple methodology provides an alternative for the synthesis of a wide range of alk-2-ynamide derivatives under mild conditions. The present protocol is ecofriendly and practical, and it shows significant recyclability.

Palladium-catalyzed oxidative aminocarbonylation by decarboxylative coupling: Synthesis of alkynyl amides

Alkynyl amides were synthesized from a palladium-catalyzed coupling reaction of alkynyl carboxylic acids and amines under carbon monoxide. The reaction was conducted with palladium(II) acetate (5 mol-%) and silver(I) oxide (1.0 equiv.) in acetonitrile at 80 °C for 1 h. This method provides good to moderate product yields and good functional group tolerance towards ketone, ester, and nitrile groups.

Palladium-N-heterocyclic carbene (NHC)-catalyzed synthesis of 2-ynamides via oxidative aminocarbonylation of alkynes with amines

A series of palladium-NHC complexes was prepared and their catalytic activity in the oxidative aminocarbonylation of alkynes with amines has been developed using oxygen as the benign oxidant, leading to an efficient approach toward the formation of a wide

Oxidative aminocarbonylation of terminal alkynes for the synthesis of alk-2-ynamides by using palladium-on-carbon as efficient, heterogeneous, phosphine-free, and reusable catalyst

Palladium-on-carbon (Pd/C)-catalyzed oxidative aminocarbonylations of alk-1-ynes with secondary amines provide the corresponding alk-2-ynamides in a good to excellent yields. This new methodology is applicable for the synthesis of a wide range of biologically active alk-2-ynamide derivatives. The developed protocol avoids the use of phosphine ligands, with an additional advantage of palladium catalyst recovery and reuse for up to four consecutive cycles. Copyright

Highly diastereo- and enantioselective aziridination of α,β-unsaturated amides with diaziridine and mechanistic consideration on its stereochemistry

During studies of aziridination of α,β-unsaturated amides with diaziridine, we found that we could prepare both the cis- and trans-aziridinecarboxamides by choosing an appropriately substituted diaziridine. While 3-monosubstituted diaziridine 2 was suitab

Rearrangements of trihalomethyl ketones

Trihalomethyl ketones have been prepared and their reactivity under basic conditions was investigated in terms of competition between 1,2- vs. 1,3-elimination and nucleophilic substitution. Favorskii rearrangement was the preferred process, but in those c