627546-31-0

Upstream product

• 603-35-0 triphenylphosphine 
• 95525-44-3 N-chloroacetyl pyrrole 
• 54582-33-1 1,1'-carbonyldiimidazole 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 19493-09-5 Methylenetriphenylphosphorane 

Downstream Products

• 736140-97-9 (2Z)-5-phenyl-1-pyrrol-1-yl-pent-2-en-1-one 
• 736140-79-7 (E)-5-phenyl-1-(1H-pyrrol-1-yl)pent-2-en-1-one 
• 736140-72-0 (E)-3-(4-chlorophenyl)-1-(1H-pyrrol-1-yl)prop-2-en-1-one 
• 736140-74-2 (2E)-3-(2-chlorophenyl)-1-pyrrol-1-yl-2-propen-1-one 
• 736140-84-4 (2E)-5-(p-methoxybenzyloxy)-1-pyrrol-1-yl-2-penten-1-one 
• 252248-89-8 N-cinnamoylpyrrole[1-(pyrrol-1'-yl)-3-phenylprop-2E-enone] 
• 949013-80-3 3-phenyl-1-pyrrol-1-yl-2-propen-1-one 
• 736140-70-8 (E)-3-(4-methoxyphenyl)-1-(1H-pyrrol-1-yl)prop-2-en-1-one 
• 736140-81-1 (E)-3-cyclohexyl-1-(1H-pyrrol-1-yl)prop-2-en-1-one 
• 736140-94-6 (2E)-(5R,6R)-7-benzyloxy-5,6-dihydroxy-5,6-O-isopropylidene-1-pyrrol-1-yl-2-heptene-1-one 

Relevant academic research and scientific papers

α,β-unsaturated N-Acylpyrrole peptidyl derivatives: New proteasome inhibitors

Because of the encouraging results obtained using vinyl ester derivatives, we synthesized and tested a novel series of peptide-based proteasome inhibitors bearing a new pharmacophore unit at the C-terminal. N-Acylpyrrole moiety is a potential substrate for Michael addition by catalytic threonine. Several analogues have demonstrated a selective inhibition of the multicatalytic complex β1 subunits, the capacity to permeate cellular membrane, and good pharmacokinetics properties.

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.

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.