67100-39-4

Upstream product

• 67347-31-3 3-Benzenesulfonyl-3-benzyl-cyclopentanol 
• 103130-88-7 tert-Butyl-dimethyl-{3-[1-phenyl-meth-(Z)-ylidene]-cyclopent-1-enyloxy}-silane 
• 100-39-0 benzyl bromide 
• 168908-06-3 (3-Methoxy-cyclopent-2-enesulfonyl)-benzene 
• 22627-70-9 3-ethoxycyclopent-2-en-1-one 
• 6921-34-2 benzylmagnesium chloride 
• 930-30-3 cyclopent-2-enone 
• 69248-37-9 2-benzylcyclopenta-1,3-diene 
• 1616976-25-0 C₂₁H₂₆O₂SSi 
• 1589-82-8 phenylmagnesium bromide 
• 3859-41-4 1,3-cyclopentadione 
• 196596-61-9 1-t-butyldimethylsiloxy-1-(3-phenyl-1,2-propadienyl)cyclopropane 
• 163224-61-1 1-(3-phenyl-1,2-propadienyl)cyclopropanol 
• 1094823-59-2 1-(3-phenylprop-1-ynyl)cyclopropanol 

Downstream Products

• 85163-16-2 3-benzylcyclopentan-1-one 
• 55007-06-2 2,3-epoxy-3-benzylcyclopentanone 
• 1383979-37-0 (2S,3R)-epoxy-3-(benzyl)cyclopentanone 

Relevant academic research and scientific papers

Enantioselective Hydrogenation of Endocyclic Enones: the Solution to a Historical Problem?

The enantioselective hydrogenation of endocyclic enones has been a historical problem for homogeneous catalysis. We herein report an efficient method to reduce endocyclic enones with molecular hydrogen. Catalyzed by a rhodium/Zhaophos complex, a variety of enones with five-, six- or seven-member ring were hydrogenated with high enantioselectivity (92%—99% ee). Excellent chemo- and enantioselectivity demonstrated this method was successfully applied in the enantioselective hydrogenation of citral to produce enantio-enriched citronellal.

Ground-State Electron Transfer as an Initiation Mechanism for Biocatalytic C-C Bond Forming Reactions

The development of non-natural reaction mechanisms is an attractive strategy for expanding the synthetic capabilities of substrate promiscuous enzymes. Here, we report an "ene"-reductase catalyzed asymmetric hydroalkylation of olefins using α-bromoketones as radical precursors. Radical initiation occurs via ground-state electron transfer from the flavin cofactor located within the enzyme active site, an underrepresented mechanism in flavin biocatalysis. Four rounds of site saturation mutagenesis were used to access a variant of the "ene"-reductase nicotinamide-dependent cyclohexanone reductase (NCR) from Zymomonas mobiles capable of catalyzing a cyclization to furnish β-chiral cyclopentanones with high levels of enantioselectivity. Additionally, wild-type NCR can catalyze intermolecular couplings with precise stereochemical control over the radical termination step. This report highlights the utility for ground-state electron transfers to enable non-natural biocatalytic C-C bond forming reactions.

Mechanism of Ru(II)-Catalyzed Rearrangements of Allenyl- and Alkynylcyclopropanols to Cyclopentenones

A comparison study of the Ru(II)-catalyzed rearrangements of allenyl- and alkynylcyclopropanols to the corresponding cyclopentenones has been undertaken with the aid of an alkyl substituent on the three-membered ring. These ring expansion reactions proceed with exceptional regioselectivity irrespective of the cis/trans stereochemistry of the substituents on the three-membered ring. β-Carbon elimination is the common feature in the absence of a chelating group at the 4′-position in the alkyne chain.

The sila-Pummerer reaction of γ-silyl substituted cycloalkanoyl sulfoxides: The first examples and a new approach to 3-substituted cycloalk-2-enones

The thermal decomposition of 3-(α-trimethylsilyl)alkyl substituted 2-(phenylsulfinyl)cycloalkanones occurs via the γ-sila-Pummerer reaction, affording 3-substituted cycloalk-2-enones and unstable trimethylsilyl benzenesulfenate as an elimination by-product. The starting γ-silyl substituted cycloalkanoyl sulfoxides were obtained through the conjugate addition reaction of nucleophilic reagents to 2-(phenylsulfinyl)cycloalk-2- enones. The tandem conjugate addition/γ-sila-Pummerer reaction investigated here provides a new route to 3-substituted cycloalk-2-enones.

Hydride reduction of alpha, beta-unsaturated carbonyl compounds using chiral organic catalysts

Nonmetallic, chiral organic catalysts are used to catalyze the 1,4-hydride reduction of an α,β-unsaturated carbonyl compound. The α,β-unsaturated carbonyl compound may be an aldehyde or cyclic ketone, and the hydride donor may be a dihydropyridine. The reaction is enantioselective, and proceeds with a variety of hydride donors, catalysts, and substrates. The invention also provides compositions effective in carrying out the 1,4-hydride addition of α,β-unsaturated carbonyl compounds.

Organocatalytic transfer hydrogenation of cyclic enones

The first enantioselective organocatalytic transfer hydrogenation of cyclic enones has been accomplished. The use of iminium catalysis has provided a new organocatalytic strategy for the enantioselective reduction of β,β-substituted α,β-unsaturated cycloalkenones, to generate β-stereogenic cyclic ketones. The use of imidazolidinone 4 as the asymmetric catalyst has been found to mediate the hydrogenation of a large class of enone substrates with tert-butyl Hantzsch ester serving as an inexpensive source of hydrogen. The capacity of catalyst 4 to enable enantioselective transfer hydrogenation of cycloalkenones has been extended to five-, six-, and seven-membered ring systems. The sense of asymmetric induction is in complete accord with the stereochemical model first reported in conjunction with the use of catalyst 4 for enantioselective ketone Diels-Alder reactions. Copyright

Titanium-mediated [4 + 1] assembly of 1,3-dienes and nitriles: Formation of 3-cyclopentenyl amines and cyclopentenones

In the presence of Ti(OiPr)4 and iPrMgCl, dienes couple with nitriles to afford the title products in good yields. The Royal Society of Chemistry 2005.

Asymmetric 1,4-reductions of hindered β-substituted cycloalkenones using catalytic SEGPHOS-ligated CuH

The reagent combination of catalytic amounts of copper hydride ligated by a nonracemic SEGPHOS ligand leads in situ to an extremely reactive species capable of effecting asymmetric hydrosilylations of conjugated cyclic enones in very high ees. An unpreced

Simple construction of bicyclo[4.3.0]nonane, bicyclo[3.3.0]octane, and related benzo derivatives by palladium-catalyzed cycloalkenylation

(equation presented) Bicyclo[4.3.0]nonanes (hydrindanes) and bicyclo[3.3.0]octanes (octahydropentalenes) are easily synthesized by palladium-catalyzed cycloalkenylations. Additionally, benzo-fused bicyclo[3.3.0]octanes are prepared for the first time thro