26965-15-1

Upstream product

• 705-60-2 1-phenyl-2-nitroprop-1-ene 
• 96-10-6 diethylaluminium chloride 
• 1730-25-2 allylmagnesium bromide 
• 24401-36-3 2-phenyl-4-penten-1-al 
• 109-64-8 1,3-dibromo-propane 
• 103-79-7 1-phenyl-acetone 
• 107-18-6 allyl alcohol 
• 109-49-9 5-Hexen-2-one 
• 841-76-9 triphenylaluminium 
• 1430406-09-9 N-methoxy-N-methyl-2-phenylpent-4-enamide 
• 75-16-1 methylmagnesium bromide 
• 14815-73-7 methyl allylphenylacetate 
• 100-59-4 phenylmagnesium chloride 
• 109-99-9 tetrahydrofuran 

Downstream Products

• 73222-64-7 (1-Isopropenyl-but-3-enyl)-benzene 
• 1173092-41-5 (3R)-3-phenyl-5-hexen-2-one 
• 2833-34-3 (S)-1-phenyl-3-buten-1-yl acetate 
• 181227-42-9 (+)-(R)-1-phenylbut-3-en-1-yl acetate 
• 36293-43-3 (2R,3S)-3-phenylhex-5-en-2-ol 
• 36293-44-4 (2R,3R)-3-phenylhex-5-en-2-ol 
• 676548-10-0 (2S,3S)-3-phenylhex-5-en-2-ol 
• 676548-09-7 (2S,3R)-3-phenylhex-5-en-2-ol 
• 132637-47-9 2-phenylhex-5-en-2-yl hydroperoxide 
• 120625-72-1 C₁₉H₁₈N₄O₆ 

Relevant academic research and scientific papers

Reactions of α,α-disubstituted selenoamides with organolithium reagents leading to unsymmetrical ketones

α,α-Disubstituted selenoamides were easily converted to unsymmetrical ketones in high yields by the reaction with alkyllithiums, whereas the reaction with alkynyllithium and methyl iodide gave α,β-unsaturated ketone and dialkynylamine.

ELECTROPHILE-INITIATED CONVERSION OF A PROSTAGLANDIN ENDOPEROXIDE MODEL COMPOUND TO THE THROMBOXANE B SKELETON

Reaction of the simplified prostaglandin endoperoxide model (1) with ferric or cupric ion afforded the lactols (2a, b) containing the thromboxane B ring moiety, along with ketol (3) and levulinaldehyde derivatives (4, 5).

The salt-free nickel-catalysed α-allylation reaction of ketones with allyl alcohol and diallylether

The nickel-catalysed α-allylation of ketones with allyl alcohol and diallylether has been performed under neutral conditions. As no base is involved, the products are synthesized without salts as side products. The dppf/Ni(cod)2 catalytic system in MeOH at 80 °C has been shown as the most effective reaction system to afford tetrasubstituted derivatives from various cyclic and acyclic ketones with one or two mobile protons. This process combined with a metathesis step yields spirocyclic compounds according to a salt free synthetic sequence.

Chiral isoxazolidine-mediated stereoselective umpolung α-phenylation of methyl ketones

An effective asymmetric α-phenylation of methyl ketones with triphenylaluminium in the presence of (+)-benzopyranoisoxazolidine has been developed. The reaction proceeds via the in situ formation of a chiral N-alkoxyenamine and the subsequent diastereoselective nucleophilic phenylation to provide α-phenylated products in moderate to good yields, with high enantioselectivities.

Stereocontrolled Synthesis of Amino-Substituted Carbocycles by Pd-Catalyzed Alkene Carboamination Reactions

Amino-substituted alkylidenecyclopentanes were synthesized through a stereoselective intermolecular Pd-catalyzed alkene carboamination reaction between alkenyl triflates bearing a pendant alkene and exogenous amine nucleophiles. The reactions are effective with a range of different substrate combinations, and proceed with generally high diastereoselectivity. Use of (S)-tBuPhox as the ligand in reactions of achiral substrates provides enantioenriched products with up to 98.5:1.5 e.r.

Dynamic Reductive Kinetic Resolution of Benzyl Ketones using Alcohol Dehydrogenases and Anion Exchange Resins

Dynamic reductive kinetic resolutions of racemic 3-arylalkanones have been performed by the proper combination of an alcohol dehydrogenase and a basic anionic resin. The best results were found for the bioreduction with the alcohol dehydrogenase type A from Rhodococcus ruber DSM 44541 overexpressed in Escherichia coli (E. coli/ADH-A) and the commercially available evo-1.1.200, while the Amberlite IRA-440 C and the DOWEX-MWA-1 resins allowed efficient in situ racemizations. Reaction conditions were optimized in terms of enzyme source and loading, type and amount of resin, pH, temperature and reaction times, obtaining a series of (R,R)-substituted propan-2-ols with good conversions and both diastereoselectivity and stereoselectivity. As a proof of concept, the subsequent intramolecular cyclization of a selected propan-2-ol substrate afforded a valuable isochroman heterocycle without any loss of the optical purity.

One-pot method for α-phenylation of ketones using isoxazolidine and triphenylaluminum

The efficient one-pot umpolung α-phenylation of ketones via N-alkenylisoxazolidine is described. When the various ketones are treated with triphenylaluminum prepared from phenylmagnesium chloride and AlCl3 in the presence of isoxazolidine, the desired products are obtained in good to moderate yield. This method is equivalent to a direct α-arylation reaction of carbonyl groups.

Deacylative allylation: Allylic alkylation via retro-Claisen activation

A new method for allylic alkylation of a variety of relatively nonstabilized carbon nucleophiles is described herein. In this process of "deacylative allylation", the coupling partners, an allylic alcohol and a ketone pronucleophile, undergo in situ retro-Claisen activation to generate an allylic acetate and a carbanion. In the presence of palladium, these reactive intermediates undergo catalytic coupling to form a new C-C bond. In comparison to unimolecular decarboxylative allylation, a commonly utilized method for allylation of carbon anions, deacylative allylation is an intermolecular process. Moreover, deacylative allylation allows the direct coupling of readily available allylic alcohols. Lastly, the full utility of deacylative allylation is demonstrated by the rapid construction of a variety 1,6-heptadienes via 3-component couplings.

Multi-product classes obtained from allylation of α-halo ketones with allylzinc bromide

An efficient, one-pot synthesis procedure for the preparation of allylic epoxides, aldehydes and homoallylic alcohols (see scheme) has been described. The three industrial products were synthesized by the reaction of allylzinc bromide with a-halo ketones

Baeyer-Villiger monooxygenase-catalyzed kinetic resolution of racemic α-alkyl benzyl ketones: enzymatic synthesis of α-alkyl benzylketones and α-alkyl benzylesters

The application of three BVMOs for the enantioselective oxidation of 3-phenylbutan-2-ones with different substituents in the aromatic moiety is described. By choosing the appropriate biocatalyst and substrate combination, chiral ketones and esters can be obtained with excellent enantiopurities. This methodology could also be applied to the resolution of racemic α-alkyl benzylketones with longer alkyl chains as well as with two substituted α-substituted benzylacetones. A kinetic analysis revealed that the BVMOs studied effectively convert all tested compounds showing that the enzymes are tolerant towards the substrate structure while being highly enantioselective. These properties render BVMOs as valuable biocatalysts for the preparation of compounds with high interest in organic synthesis.