84846-41-3

Upstream product

• 108-24-7 acetic anhydride 
• 25746-83-2 (2S)-N-phenylpyrrolidine-2-carboxamide 
• 62-53-3 aniline 
• 68-95-1 (S)-acetylproline 
• 143063-89-2 para-ethylphenyl isocyanide 
• 1148-11-4 N-Benzyloxycarbonyl-L-proline 
• 64030-42-8 benzyl (2S)-2-(phenylcarbamoyl)pyrrolidine-1-carboxylate 

Downstream Products

• 84846-47-9 (S)-2-(anilinomethyl)-1-ethylpyrrolidine 

Relevant academic research and scientific papers

Synthesis of amides by palladium-catalyzed decarbonylative coupling of carboxylic acids with isocyanides

Amides were synthesized from carboxylic acids and isocyanides under Pd II/AgI/base catalytic conditions. The reaction conditions were optimized, and the scope was studied. Various carboxylic acids and aryl isocyanides are compatible with this reaction, but alkyl isocyanides are not. A plausible mechanism, which features distinctive PdII-mediated decarbonylative coupling and unprecedented nucleophilic attack of carboxylates to PdII-ligated isocyanides, was proposed to account for this reaction. N-Arylamides are assembled in high yields from carboxylic acids and isocyanides under PdII/AgI/base catalytic conditions. The decarbonylative coupling features unprecedented nucleophilic attack of the carboxylate on the isocyanide, which acts as an electrophile as a result of its coordination to PdII, and this inverted reactivity is proposed to account for this transformation.

A simple proline-based organocatalyst for the enantioselective reduction of imines using trichlorosilane as a reductant

A simple and inexpensive proline-based organocatalyst was developed for the reduction of imines using trichlorosilane as a reductant. The reduction of N-aryl imines in the presence of 10 mol % of N-pivaloyl-l-proline anilide was carried out to give the co

Enantioselective addition of diethylzinc to aldehydes catalyzed by (S)-1-alkyl-2-(arylamino)methylpyrrolidine

Several chiral diamines, (S)-1-alkyl-2-(arylamino)methylpyrrolidine, were used as chiral catalysts for the enantioselective addition of diethylzinc to aldehydes. The best results were obtained by employing 0.15 equiv of (S)-2-anilinomethyl-1-benzylpyrrolidine, and chiral secondary alcohols were obtained with high enantiomeric excesses (up to 94% ee).

Recognition of achiral and chiral ammonium salts by neutral ditopic receptors based on chiral salen-UO2 macrocycles

(Figure Presented) A mononuclear (M20) and a dinuclear (M40) uranyl chiral macrocyclic complex, incorporating both a salen unit containing two phenyl rings linked to a chiral diimine bridge and the (R)-BINOL unit, behaves as an efficient ditopic receptor for achiral and chiral quaternary ammonium salts. Binding affinities in chloroform solution have been measured for 1:1 complexes of many quaternary salts encompassing tetramethylammonium (TMA), tetraethylammonium (TEA), tetrabutylammonium (TBA), and acetylcholine (ACh), as well as trimethylanilinium (TriMAn), benzyltrimethylammonium (BnTriMA), (a-methylbenzyl)trimethylammonium and pyrrolidinium cations. The anion of the salt is bound by the hard Lewis acidic uranyl site, with an increasing binding efficiency on increasing the anion hardness (I- - -), whereas CH-π or π-π attractions by binapthyl moiety, or the salicylaldehyde unit, or the phenyl rings of diimine bridge ensure the recognition of the cation partner. Optimized structures of receptor-anion-cation ternary complexes obtained by MM calculations are supported by 2D-ROESY NMR measurements.

The Enantioselective Michael Addition of Thiols to Cycloalkenones by Using (2S,4S)-2-Anilinomethyl-1-ethyl-4-hydroxypyrrolidine as Chiral Catalyst

Catalytic asymmetric addition of thiols to 2-cycloalkenone was studied by using the chiral amino alcohols, derived from L-hydroxyproline or (S)-proline, as base catalysts.Detailed investigation was carried out on the effects of the structure of the cataly