469873-54-9

Upstream product

• 3417-91-2 L-tyrosine methyl ester HCl 
• 109-73-9 N-butylamine 
• 67-64-1 acetone 
• 40829-19-4 (2S)-2-amino-N-butyl-3-(4-hydroxyphenyl)propanamide 
• 1080-06-4 L-Tyr-OMe 
• 60-18-4 L-tyrosine 

Downstream Products

• 1312022-94-8 (5S)-3-butyl-2,2-dimethyl-5-{[4-(prop-2-yn-1-yloxy)phenyl]methyl}imidazolidin-4-one 
• 1312022-95-9 C₂₅H₄₁N₅O₅Si 
• 1621327-43-2 (S)-5-[4-(benzyloxy)benzyl]-3-butyl-2,2-dimethylimidazolidin-4-one 
• 1621327-44-3 (S)-3-butyl-2,2-dimethyl-5-[4-(perfluorobenzyloxy)benzyl]imidazolidin-4-one 
• 1621327-45-4 (S)-3-butyl-2,2-dimethyl-5-[4-(pyren-1-ylmethoxy)-benzyl]imidazolidin-4-one 
• 1446101-10-5 C₂₂H₃₈N₂O₅Si 
• 1364703-09-2 C₁₉H₂₈N₂O₂ 

Relevant academic research and scientific papers

A Continuous-Flow, Two-Step, Metal-Free Process for the Synthesis of Differently Substituted Chiral 1,2-Diamino Derivatives

The enantioselective organocatalytic reduction of aryl-substituted nitroenamines was successfully performed under continuous-flow conditions. After a preliminary screening with a 10-μL microreactor, to establish the best reaction conditions, the reduction was scaled up in a 0.5-mL mesoreactor, without appreciable loss of enantioselectivity, that remained constantly higher than 90%. The in-flow nitro reduction was also accomplished, either by Raney nickel catalyzed hydrogenation or by a metal-free methodology based on the use of the very inexpensive and readily available reducing agent trichlorosilane. The final aim is to develop a two-step, continuous-flow process for the stereoselective, metal-free, catalytic synthesis of differently functionalized chiral 1,2-diamines.

Hydrogel supported chiral imidazolidinone for organocatalytic enantioselective reduction of olefins in water

Chiral products play an important role particularly in the field of medicinal chemistry, where it is known that enantiomers often have very different biological properties and effects. One of the most powerful tool to obtain a product as a single enantiomer is asymmetric catalysis. Recently, organocatalysis, i.e. the use of small organic molecules to catalyze enantioselective transformations, has emerged as a prominent field in asymmetric synthesis. In this work, the use of hydrogels as a support for a chiral imidazolidinone organocatalyst (MacMillan catalyst) and its application in the reduction of activated olefins mediated by the Hantzsch ester is reported for the first time. Results showed a good activity of hydrogels in respect to both yield and enantioselection.

A chiral organocatalytic polymer-based monolithic reactor

Radical copolymerisation of divinylbenzene and a properly modified enantiomerically pure imidazolidinone inside a stainless steel column in the presence of dodecanol and toluene as porogens afforded the first example of a chiral organocatalyst immobilized

Stereoselective Diels-Alder reactions promoted under continuous-flow conditions by silica-supported chiral organocatalysts

Silica nanoparticles of different morphological properties were functionalized with enantiomerically pure imidazolidinones, through different immobilization techniques; stainless-steel columns were then loaded with silica bearing chiral organocatalysts to

Continuous-flow stereoselective organocatalyzed Diels-Alder reactions in a chiral catalytic "homemade" HPLC column

Continuous-flow organocatalyzed Diels-Alder reactions have been performed with excellent enantioselectivity for the first time in a chiral "homemade" HPLC column, packed with silica on which a MacMillan catalyst has been supported by a straightforward imm

Chiral hybrid inorganic-organic materials: Synthesis, characterization, and application in stereoselective organocatalytic cycloadditions

The synthesis of chiral imidazolidinones on mesoporous silica nanoparticles, exploiting two different anchoring sites and two different linkers, is reported. Catalysts 1-4 were prepared starting from l-phenylalanine or l-tyrosine methyl esters and support

Recyclable tetraarylphosphonium supported chiral imidazolidin-4-one organocatalyst for Diels-Alder reactions

The tetraarylphosphonium supported chiral imidazolidin-4-ones were synthesized and used to catalyze the Diels-Alder reactions of cyclopentadiene and α,β-unsaturated aldehydes. High enantiomeric excesses and good yields were obtained, and catalyst recyclin

Poly(methylhydrosiloxane)-supported chiral imidazolinones: New versatile, highly efficient and recyclable organocatalysts for stereoselective Diels-Alder cycloaddition reactions

Poly(methylhydrosiloxane) (PMHS) supported organic catalysts promoted the Diels-Alder reaction of dienes with α,β-unsaturated aldehydes, also in pure water, in yields and enantiomeric excesses comparable to those observed with the non-supported catalysts

A click strategy for the immobilization of macmillan organocatalysts onto polymers and magnetic nanoparticles

A chemically modified, first generation MacMillan imidazolidin-4-one has been anchored onto 1% DVB Merrifield resin and Fe3O4 (5.3 ± 1.4 nm) magnetic nanoparticles through copper-catalyzed alkyne azide cycloaddition (CuAAC) reactions. The resulting immobilized catalysts have been successfully used in the asymmetric Friedel-Crafts alkylation of N-substituted pyrroles with α,β-unsaturated aldehydes. The PS-supported catalyst (B) showed higher catalytic activity and enantioselectivity, while the MNP-supported one (A) showed higher recyclability and could be used in a sequential process with intermediate magnetic decantation.

Heterogeneous organocatalysis at work: Functionalization of hollow periodic mesoporous organosilica spheres with MacMillan catalyst

We report a new method for the synthesis of hollow-structured phenylene-bridged periodic mesoporous organosilica (PMO) spheres with a uniform particle size of 100-200 nm using α-Fe2O3 as a hard template. Based on this method, the hollow-structured phenylene PMO could be easily functionalized with MacMillan catalyst (H-PhPMO-Mac) by a co-condensation process and a "click chemistry" post-modification. The synthesized H-PhPMO-Mac catalyst has been found to exhibit high catalytic activity (98 % yield, 81 % enantiomeric excess (ee) for endo and 81 % ee for exo) in asymmetric Diels-Alder reactions with water as solvent. The catalyst could be reused for at least seven runs without a significant loss of catalytic activity. Our results have also indicated that hollow-structured PMO spheres exhibit higher catalytic efficiency than solid (non-hollow) PMO spheres, and that catalysts prepared by the co-condensation process and "click chemistry" post-modification exhibit higher catalytic efficiency than those prepared by a grafting method.