73893-85-3

Upstream product

• 93-55-0 1-phenyl-propan-1-one 
• 2114-00-3 2-bromo-1-phenyl-1-propanone 
• 2564-83-2 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical 
• 591-51-5 phenyllithium 
• 107-02-8 acrolein 
• 37471-46-8 1-phenyl-1-trimethylsiloxypropene 
• 66323-99-7 trimethyl[(Z)-(1-phenyl-1-propenyl)oxy]silane 
• 131770-31-5 N-(4-Chlorophenyl)glycine methyl ester 
• 34733-55-6 (2R*,3R*)-2,3-dimethyl-1,4-diphenylbutane-1,4-dione 
• 120331-99-9 (Z)-9-(1-phenylprop-1-enyloxy)-9-borabicyclo[3.3.1]nonane 
• 768-03-6 Phenyl vinyl ketone 
• 18649-43-9 4-methoxyphenyllead(IV) triacetate 
• 6622-76-0 methyl (E)-2-methyl-2-butenoate 
• 30085-70-2 [E]-1-morpholino-1-phenyl-1-propene 

Downstream Products

• 17799-61-0 3,4-dimethyl-2,5-diphenyl-1H-pyrrole 
• 51181-43-2 3,4-Dimethyl-2,5-diphenylfuran 
• 147677-43-8 meso-2,5-diphenyl-3,4-dimethylhexa-1,5-diene 
• 137596-51-1 3,4-dimethyl-2,5-diphenyl-1-(2-hydroxyethyl)pyrrole 

Relevant academic research and scientific papers

Electrochemical and Photocatalytic Oxidative Coupling of Ketones via Silyl Bis-enol Ethers

Diastereoselective oxidative coupling of ketones through a silyl bis-enol ether intermediate by anodic and photocatalytic oxidation is reported. These methods provide several 1,4-diketones in good yields without the need for stoichiometric metal oxidants. The strategic use of a silicon tether enables the coupling of both aromatic and aliphatic ketones as well as the synthesis of quaternary centers. Cyclic voltammetry is used to gain insight into the oxidation events of the reaction.

Visible-Light-Enabled Enantioconvergent Synthesis of α-Amino Acid Derivatives via Synergistic Br?nsted Acid/Photoredox Catalysis

An unprecedented radical cross-coupling reaction was achieved between glycine esters and racemic α-bromoketones catalyzed by synergistic Br?nsted acid/photoredox catalysis, thus serving as an efficient platform for the synthesis of highly valuable enantioenriched unnatural α-amino acid derivatives. This dual catalysis provides a powerful capability to control the reactive radical intermediate and iminium ion, thereby enabling enantioconvergent bond-formation in a highly stereochemical manner. An array of valuable enantioenriched unnatural α-amino acid derivatives bearing two contiguous stereogenic centers are readily accessible with high diastereoselectivity and excellent enantioselectivity, which include α-amino acids with a unique β-fluorinated quaternary stereocenter or its β-all-carbon counterpart. A strong chiral amplification effect was observed in this dual catalytic system.

Bioinspired total synthesis of tetrahydrofuran lignans by tandem nucleophilic addition/redox isomerization/oxidative coupling and cycloetherification reactions as key steps

A very short three-step approach to trans,trans,trans-2,5-diaryl-3,4-dimethyltetrahydrofuran lignans is reported. The carbon skeleton is assembled in a single step based on an unprecedented tandem reaction consisting of 1,2-addition of aryllithium reagents to α,β-unsaturated aldehydes, ruthenium-catalyzed redox isomerization of the resulting alkoxides to enolates and their dimerization triggered by single electron oxidation. The resulting 2,3-dialkyl-1,4-diketones form with moderate to good d/l-diastereoselectivity and are transformed to the target tetrahydrofuran lignans by reduction and diastereoselective cycloetherification.

Cross-coupling of dissimilar ketone enolates via enolonium species to afford non-symmetrical 1,4-diketones

Due to their closely matched reactivity, the coupling of two dissimilar ketone enolates to form a 1,4-diketone remains a challenge in organic synthesis. We herein report that umpolung of a ketone trimethylsilyl enol ether (1 equiv) to form a discrete enol

Oxovanadium(v)-induced diastereoselective oxidative homocoupling of boron enolates

Oxovanadium(v)-induced dl-selective oxidative coupling of (Z)-boron enolate was demonstrated to give the corresponding 2,3-disubstituted 1,4-diketone in a good yield. High selectivity (up to 94:6) was attained when the reaction was performed with VO(OPr-i)2Cl at -30 °C. The Royal Society of Chemistry 2014.

General and efficient α-oxygenation of carbonyl compounds by TEMPO induced by single-electron-transfer oxidation of their enolates

A generally applicable method for the synthesis of protected α-oxygenated carbonyl compounds is reported. It is based on the single-electron-transfer oxidation of easily generated enolates to the corresponding α-carbonyl radicals. Coupling with the stable free radical TEMPO provides α-(piperidinyloxy) ketones, esters, amides, acids or nitriles in moderate-to-excellent yields. Enolate aggregates influence the outcome of the oxygenation reactions significantly. Competitive reactions have been analyzed and conditions for their minimization are presented. Chemoselective reduction of the products led to either N-O bond cleavage to α-hydroxy carbonyl compounds or reduction of the carbonyl functionality tomonoprotected 1,2-diols or O-protected amino alcohols. The oxygenation of enolates proves to be the most general and effective methodology for the synthesis of O-protected α-oxy carbonyl compounds and nitriles A. The scope and limitations of the electron-transfer-induced radical coupling reaction with TEMPO are presented. The reaction pathways are outlined. Methods for the deprotection to α-hydroxy carbonyl compounds B are provided and discussed. Copyright

DICARBONYL DERIVATIVES AND METHODS OF USE

Derivatives of dicarbonyl compounds having antitumor and antibiotic activity which can be used as anticancer agents.

Photoinduced electron-transfer cope rearrangements of 3,6-diaryl-2,6- octadienes and 2,5-diaryl-3,4-dimethyl-1,5-hexadienes: Stereospecificity and an unexpected formation of the bicyclo[2.2.0]hexane Derivatives

Under the 9,10-dicyanoanthracene-sensitized photoinduced electron- transfer conditions, (Z,Z)-, (E,E)-, (E,Z)-3,6-diaryl-2,6-octadiene and (d,l),(meso)-2,5-diaryl-3,4-dimethyl-1,5-hexadiene stereospecifically undergo the Cope rearrangement to give a Cope

Diastereo- and enantioselective synthesis of syn-2,3-disubstituted 1,4-diketones via oxidative coupling of metalated hydrazones

An efficient diastereo- and enantioselective synthesis of syn-2,3-disubstituted 1,4-diketones 4 is described. Key step of the procedure is the oxidative coupling of the metalated SAMP/RAMP-hydrazones 2 with iodine, followed by oxidative cleavage of the dimerized bishydrazones 3 with ozone and subsequent separation of the minor meso-isomer by chromatography. The d,l-isomers of the title 1,4-diketones 4 are obtained in good overall yields (20-64%) and high diastereo- and enantiomeric excesses (de ≥ 98%, ee = 80 - ≥95%).