169892-12-0

Upstream product

• 20913-05-7 (Benzoylmethylene)triphenylphosphorane 
• 142-29-0 cyclopentene 
• 70-11-1 α-bromoacetophenone 
• 6048-29-9 triphenylphenacylphosphonium bromide 
• 532-27-4 1-chloroacetophenone 
• 1678-18-8 (2-oxo-2-phenylethyl)-triphenylphosphonium chloride 
• 50789-30-5 5,5-dimethoxypentanal 
• 111-30-8 Glutaraldehyde 

Downstream Products

• 514167-97-6 (2E,7E)-9-oxo-9-phenyl-nona-2,7-dienoic acid methyl ester 
• 347376-17-4 trans,trans-7-acetyl-1-benzoyl-1,6-heptadiene 
• 1443014-20-7 (2R,6S)-2-(tert-butyloxycarbonylaminomethyl)-6-(2-oxo-2-phenylethyl)tetrahydro-2H-pyran 
• 1443014-05-8 (2R,6S)-2-nitromethyl-6-(2-phenyl-2-oxoethyl)tetrahydro-2H-pyran 
• 1429619-26-0 C₁₄H₁₇NO₄ 
• 1443014-04-7 C₁₄H₁₇NO₄ 
• 1646293-45-9 (1R,2S,3R,4R)-3-nitro-4-(2-oxo-2-phenylethyl)-2-phenylcyclohexanecarbaldehyde 

Relevant academic research and scientific papers

Dual catalyst control in the enantioselective intramolecular Morita-Baylis-Hillman reaction

(Chemical Equation Presented) The intramolecular Morita-Baylis Hillman (MBH) reaction has been achieved with unprecedented levels of enantioselectivity. Using a cocatalyst system involving pipecolinic acid and N-methylimidazole, cyclic MBH products have b

An intramolecular Baylis-Hillman reaction catalysed by secondary amines

Treatment of enonealdehydes 4 or 7 with a catalytic amount of a secondary amine lead to the formation of the cyclopentenol 5 or cyclohexenol 8 respectively. Piperidine proved to be the most effective catalyst for this process.

Stereoselective Visible-Light Catalyzed Cyclization of Bis(enones): A Viable Approach to the Synthesis of Enantiomerically Enriched Cyclopentane Rings

Photoredox catalytic cyclization of aryl enones in the presence of visible light, promoted either by metals or organic dyes, represent a valuable strategy for the synthesis of cycloalkanes. The development of a stereoselective version of such transformation, in the presence of the metal-free catalyst Eosin Y was studied, with the aim to realize an efficient protocol for the in-flow synthesis of enantiomerically enriched functionalized cyclopentane rings, taking advantage of the flow reactors technology. The use of a chiral auxiliary on the bisenone to be cyclized offers a straightforward and convenient option to exert a stereocontrol on the light-driven cyclization. By exploiting Evans’ oxazolidinones, the stereoselective light-driven cyclization affords, after the removal of the chiral auxiliary, a functionalized 1,2-trans cyclopentane ring in up to 83/17 enantiomeric ratio. When the reaction was performed in continuo, in a homemade coil photoreactor, high yields were observed. The cyclization was also successfully realized in a 3D-printed mesoreactor, without any change in the diastereoseletctivity of the process.

Stereoselective Synthesis of 3-Oxabicyclo[3.3.1]Nonan-2-Ones via a Domino Reaction Catalyzed by Modularly Designed Organocatalysts

A highly stereoselective method for the synthesis of functionalized 3-oxabicyclo[3.3.1]nonan-2-one derivatives with four contiguous stereogenic centers, including one tetrasubstituted stereogenic center, was realized through an organocatalytic domino Mich

Intramolecular Tandem Seleno-Michael/Aldol Reaction: A Simple Route to Hydroxy Cyclo-1-ene-1-carboxylate Esters

Intramolecular tandem seleno-Michael/aldol reaction followed by an oxidation-elimination process can be an efficient tool for the construction of hydroxy cyclo-1-ene-1-carboxylate esters from oxo-α,β-unsaturated esters. Generation of lithium selenolate from elemental selenium and n-BuLi provides a simple and efficient one-pot access to cyclic endo-Morita-Baylis-Hillman adducts.

Development of a cysteine-catalyzed enantioselective rauhut-currier reaction

Herein, we report a full account of the development of an enantioselective Rauhut-Currier process that affords products in high yields and enantioselectivities using a cysteine-based catalyst. While traditional Morita-Baylis-Hillman catalysts were found to be essentially ineffective, various derivatives of protected cysteine were found to exhibit extraordinary reactivity and enantiotopic control. Extensive screening of reaction conditions led us to discover the enhanced effects of water as an additive and the chelating power of potassium in achieving higher enantiomer ratios. Mechanistic experiments also provided insight on the potential mechanism of the reaction in addition to possible transition states that provide the absolute stereochemistry formed in the observed products. Also included is a brief survey of the reaction scope involving different ring sizes as well as functionalized substrates.

Assessing the scope of the tandem Michael/intramolecular aldol reaction mediated by secondary amines, thiols and phosphines

The outcome of a tandem Michael/intramolecular aldol reaction which is mediated by secondary amines, thiols and phosphines has been found to be highly substrate dependent, with the best results being obtained for the formation of 5 and 6-membered rings using thiol or thiolate nucleophiles. Amine and phosphine mediated cyclisations were found to be problematic in several cases but were still effective methods for the formation of 5-7 membered rings.

Synthesis of carbocycles by enone-selective reduction using organoiodotin hydride

By using di-n-butyliodotin hydride (n-Bu2SnIH), carbocycles were prepared from substrates bearing both enone and formyl moieties, where the enone-selective reduction was followed by a diastereoselective intramolecular aldol reaction. (C) 2000 Elsevier Science Ltd.

Synthesis of nitrogen heterocycles by intramolecular Michael type of amination via reduction of imines with di-n-butyliodotin hydride (n-Bu2SnIH)

(matrix presented). Novel nitrogen heterocycles were prepared by a one-pot procedure involving the reductive amination of the bifunctional substrates containing an aldehyde and enone groups with di-n-butyliodotin hydride (n-Bu2SnIH).