736140-79-7

Upstream product

• 864953-57-1 diethyl 2-oxo-2-(pyrrol-1-yl)ethylphosphonate 
• 104-53-0 3-phenyl-propionaldehyde 
• 54582-33-1 1,1'-carbonyldiimidazole 
• 627546-31-0 1-(1H-pyrrol-1-yl)-2-(triphenylphosphoranylidene)ethanone 

Downstream Products

• 1608108-66-2 ((1S,2S,3R)-4-methylene-2-phenethyl-3-((trimethylsilyl)ethynyl)cyclopentyl)(1H-pyrrol-1-yl)methanone 
• 1071992-34-1 C₁₈H₂₁NO 
• 1021867-84-4 3-(nitromethyl)-5-phenyl-1-pyrrol-1-yl-pentan-1-one 
• 864953-68-4 ((2S,3R)-3-phenethylaziridin-2-yl)(1H-pyrrol-1-yl)methanone 
• 154428-47-4 (2R,3R)-trans-2,3-epoxy-5-phenyl-1-pentanol 
• 864953-61-7 (R)-3-methoxyamino-5-phenyl-1-pyrrol-1-yl-pentan-1-one 

Relevant academic research and scientific papers

Palladium-catalyzed conjugate allylation reactions of α,β- unsaturated N- acylpyrroles

(Chemical Equation Presented) Conjugate allylation reactions of α,β-unsaturated N-acylpyrroles using allylboronic ester are catalyzed by a palladium complex that is ligated by a bidentate N-heterocyclic carbene. A variety of functional groups are tolerate

Epi-cinchona based thiourea organocatalyst family as an efficient asymmetric Michael addition promoter: Enantioselective conjugate addition of nitroalkanes to chalcones and α,β-unsaturated N-acylpyrroles

(Chemical Equation Presented) A small set of easily available epi-cinchona based thiourea organocatalysts have been synthesized and tested in enantioselective Michael addition of nitroalkanes to chalcones. These bifunctional catalyst systems promoted the

Catalytic asymmetric epoxidation of α,β-unsaturated N-acylpyrroles as monodentate and activated ester equivalent acceptors

Catalytic asymmetric epoxidation of α,β-unsaturated N-acylpyrroles as monodentate and activated ester equivalent acceptors is described. A Sm(O-i-Pr)3/(R)-H8-BINOL complex promoted the epoxidation reaction to afford products in high yield (up to quant) and high enantiomeric excess (up to >99.5% ee). Reaction proceeded smoothly using cumene hydroperoxide (CMHP) with low explosive hazard, and completed within 0.2-0.5 h with 5 mol % catalyst. Catalyst loading was successfully reduced to as little as 0.02 mol %. The N-acylpyrrole properties as well as efficient synthesis of α,β-unsaturated N-acylpyrroles are also described.

Lewis acid-Lewis acid heterobimetallic cooperative catalysis: Mechanistic studies and application in enantioselective Aza-Michael reaction

The full details of a catalytic asymmetric aza-Michael reaction of methoxylamine promoted by rare earth-alkali metal heterobimetallic complexes are described, demonstrating the effectiveness of Lewis acid-Lewis acid cooperative catalysis. First, enones we

Catalytic asymmetric 1,4-addition reactions using α,β- unsaturated N-acylpyrroles as highly reactive monodentate α,β- unsaturated ester surrogates

Synthesis and application of α,β-unsaturated N-acylpyrroles as highly reactive, monodentate ester surrogates in the catalytic asymmetric epoxidation and Michael reactions are described. α,β-Unsaturated N-acylpyrroles with various functional groups were synthesized by the Wittig reaction using ylide 2. A Sm(O-i-Pr)3/H8-BINOL complex was the most effective catalyst for the epoxidation to afford pyrrolyl epoxides in up to 100% yield and >99% ee. Catalyst loading was successfully reduced to as little as 0.02 mol % (substrate/catalyst = 5000). The high turnover frequency and high volumetric productivity of the present reaction are also noteworthy. In addition, a sequential Wittig olefination-catatytic asymmetric epoxidation reaction was developed, providing efficient one-pot access to optically active epoxides from various aldehydes in high yield and ee (96→99%). In a direct catalytic asymmetric Michael reaction of hydroxyketone promoted by the Et 2Zn/linked-BINOL complex, Michael adducts were obtained in good yield (74-97%), dr (69/31-95/5), and ee (73-95%). This represents the first direct catalytic asymmetric Michael reaction of unmodified ketone to an α,β-unsaturated carboxylic acid derivative. The properties of α,β-unsaturated N-acylpyrrole are also discussed. Finally, the utility of the N-acylpyrrole unit for further transformations is demonstrated.

Sequential Wittig olefination-catalytic asymmetric epoxidation with reuse of waste Ph3P(O): Application of α,β-unsaturated N-Acyl pyrroles as ester surrogates

Waste not, want not: Efficient one-pot access to optically active epoxides with 96 to 99.5% ee from a variety of aldehydes is described. In a sequential process, the Ph3P(O) by-product of a Wittig reaction acts as a modulator for the samarium catalyst in the asymmetric epoxidation of the conjugated N-acyl pyrrole Wittig product (see scheme). The N-acyl pyrrole functionality is key to the high reactivity and selectivity observed. R = alkyl, aryl, vinyl.