102285-89-2

Upstream product

• 100-52-7 benzaldehyde 
• 120-92-3 cyclopentanone 
• 1056246-36-6 2-bromocyclopentanone 
• 930-30-3 cyclopent-2-enone 
• 75-77-4 chloro-trimethyl-silane 
• 19980-43-9 1-(trimethylsilyloxy)cyclopentene 
• 134749-87-4 2-(2-trimethylsilanylphenyl)-1,3-dioxolane 
• 37160-52-4 lithium cyclopent-1-enolate 
• 219583-51-4 trichloro<(cyclopentenyl)oxy>silane 
• 17887-55-7 2-trimethylsilylbenzaldehyde 
• 694-28-0 2-chlorocyclopentanone 
• 372493-23-7 1-trimethoxysilyloxycyclopentene 
• 109863-09-4 (1-cyclopentenyloxy)dimethoxyborane 
• 693-03-8 n-butyl magnesium bromide 

Downstream Products

• 131923-99-4 (E)-6-Phenyl-hex-5-enoic acid 2-hydroxy-ethyl ester 
• 1921-90-0 2-benzylidenecyclopentanone 
• 1921-90-0 (E)-2-benzylidenecyclopentanone 

Relevant academic research and scientific papers

The (S)-proline/polyelectrolyte system: An efficient, heterogeneous, reusable catalyst for direct asymmetric aldol reactions

A direct asymmetric aldol reaction between unmodified aldehydes and ketones was achieved using the (S)-proline/poly-(diallyldimethylammonium) hexafluorophosphate heterogeneous catalytic system with enantioselectivities and yields comparable to those obtained in the (S)-proline-catalyzed reactions performed under homogeneous conditions. Recycling of the catalyst was possible at least six times without loss of activity and enantioselectivity. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Reusable shuttles for exchangeable functional cargos: Reversibly assembled, magnetically powered organocatalysts for asymmetric aldol reactions

A supramolecular approach has been followed to support adamantyl substituted proline organocatalysts onto the surface of magnetite nanoparticles decorated with a β-cyclodextrin motif. The resulting magnetic nanoparticles (ca. ～10 nm diameter) were used as modular, magnetically recyclable catalysts in the asymmetric aldol reaction of aromatic aldehydes with cyclic ketones in water. The catalytic assemblies can be easily dismantled in organic media, and the recovered nanoparticles (magnetically powered chemical shuttles) re-complexed with another suitably substituted catalytic unit (replaceable functional cargo).

Yb(OTf)3-TMSCl, a novel catalytic system in cross-aldol reactions

A combination of Yb(OTf)3 and TMSCl influenced the outcome of cross-aldol reactions of cycloalkanones and benzaldehyde. Interestingly, reaction of cycloheptanone and cyclooctanone with aldehydes under the Yb(OTf)3- TMSCl reagent system provides 3-(2-oxocycloalkyl)-3- phenylpropanals in conjunction with the corresponding aldol products.

Development of highly enantioselective asymmetric aldol reaction catalyzed by 1-glycyl-3-methyl imidazolium chloride-iron(III) complex

A novel, effective asymmetric 1-glycyl-3-methyl imidazolium chloride-iron(III) [[Gmim]Cl-Fe(III)] complex was synthesized and studied as organocatalyst in asymmetric aldol addition under solvent free condition at 25 C. The hydrophobic group of amino acid

Methyl 12-[d-prolinoylamino]cholate as a versatile organocatalyst for the asymmetric aldol reaction of cyclic ketones

The use of cholic acid derivative 1, bearing a d-prolinamide moiety linked at the 12-position of cholic acid methylester, as an organocatalyst in the asymmetric aldol reaction of cyclic ketones and aromatic aldehydes, gave the corresponding aldol products in good yield and ee up to 98%. This organocatalyst has proven to be efficient both in water and in organic solvent, where it has been used with a 1% loading.

A recyclable non-immobilized siloxy serine organocatalyst for the asymmetric direct aldol reaction

A recyclable siloxy-l-serine organocatalyst has been developed to catalyze asymmetric direct aldol reactions in [bmim][BF4], furnishing the β-hydroxy carbonyl scaffold in high enantio- and diastereoselectivities using a selection of aromatic al

Dried chitosan-gels as organocatalysts for the production of biomass-derived platform chemicals

Aldol condensations between sugar-derived dehydrated aldehydes (e.g. furfural) and acetone have been proposed as a route to provide useful biomass-derived chemicals. In the quest of sustainable catalytic ways for such aldol condensations, this paper assesses the use of dried chitosan-gels as naturally-immobilized, readily available and non-hazardous amino-based organocatalysts. At room temperature chitosan dried gels are not suitable catalysts for the desired reaction. However, at higher temperatures (>90 °C) reaction proceeds efficiently either in solvent-free systems (with addition of catalytic amounts of water) or in water. The set-up of closed reactor set-ups (thermoshakers or microwave reactions) proved highly beneficial for the reaction outcome. Furthermore, chitosan dried gels were successfully re-used for a number of cycles. An efficient catalyst drying method (either lyophilization or scCO2 drying) was crucial to achieve virtually full conversions in 4 h. After pertinent further process optimization, dried chitosan-gels may become very useful catalysts for their use in biomass-based reactions in biorefineries.

Highly Enantio- and Diastereoselective l -Proline Derived Acetylglucose Amide Catalyzed Aldol Reaction of Ketones to Aldehydes under Solvent-Free Conditions

A novel organocatalyst was developed from d-glucosamine and l-proline, which was shown to catalyze the direct aldol reaction of ketones with aldehydes in a highly diastereoselective and enantioselective manner under solvent-free conditions. The presence o

Asymmetric aldol additions catalyzed by chiral phosphoramides: Electronic effects of the aldehyde component

The trichlorosilyl enolates of cyclopentanone and cycloheptanone were prepared by a mercury(II)-catalyzed metathesis from their TMS enol ethers in good yield. These enolates undergo spontaneous addition to aldehydes to provide the aldol adducts syn-4, 5a-

L-proline in an ionic liquid as an efficient and reusable catalyst for direct asymmetric aldol reactions

L-proline in imidazolium-based ionic liquids has been successfully used as an efficient and reusable catalyst for direct asymmetric aldol reactions.