73057-40-6

Upstream product

• 68-12-2 N,N-dimethyl-formamide 
• 766-97-2 4-n-methylphenylacetylene 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 624-31-7 4-tolyl iodide 
• 19012-03-4 N-methyl-3-formylindole 
• 60512-56-3 1-(2,2-dibromovinyl)-4-methylbenzene 
• 104-87-0 4-methyl-benzaldehyde 
• 107-19-7 propargyl alcohol 
• 16017-24-6 3-p-tolylprop-2-yn-1-ol 
• 62358-86-5 1-(3,3-diethoxyprop-1-ynyl)-4-methylbenzene 

Downstream Products

• 919087-42-6 1-(4,4-dibromobut-3-en-1-ynyl)-4-methylbenzene 
• 1022915-11-2 1-phenyl-N-(3-p-tolylprop-2-ynylidene)methanamine oxide 
• 1026667-48-0 1-p-tolyl-hex-5-en-1-yn-3-ol 
• 1220194-13-7 (R)-6-chloro-4-nitromethyl-2-p-tolyl-4H-chromene-3-carbaldehyde 
• 1220194-15-9 (R)-6-methoxy-4-nitromethyl-2-p-tolyl-4H-chromene-3-carbaldehyde 
• 1221590-70-0 C₂₀H₁₈O₂ 
• 1232144-19-2 (S)-methyl-3-(6-((tert-butyldimethylsilyloxy)methyl)-3-hydroxy-4-oxo-4H-pyran-2-yl)-3-p-tolylpropanoate 
• 1241601-80-8 (E)-1-(2-styrylphenyl)-3-p-tolylprop-2-yn-1-ol 
• 1254213-01-8 (R) ethyl 3-formy-4-hydroxy-7-methoxy-2-p-tolyl-4H-chromene-4-carboxylate 
• 1261120-05-1 ethyl 6-methyl-2-oxo-4-p-tolyl-3,4-dihydro-2H-pyran-5-carboxylate 
• 1253185-83-9 C₁₁H₉NO 
• 1322081-00-4 ethyl (R)-6-methyl-2-oxo-4-(p-tolyl)-3,4-dihydro-2H-pyran-5-carboxylate 
• 1314146-59-2 1-(2-(2-hydroxy-4-p-tolylbut-3-ynyl)-1-methyl-1H-indol-3-yl)-2-methylpropan-1-one 
• 1314146-75-2 1-(3-isobutyryl-1-methyl-1H-indol-2-yl)-4-p-tolylbut-3-yn-2-one 

Relevant academic research and scientific papers

Addition of diethylzinc to dicobalt hexacarbonyl complexes of α,β-acetylenic aldehydes with virtually complete enantioselectivity. A formal synthesis of (+)-incrustoporin

(Matrix presented) The addition of diethylzinc to dicobalt hexacarbonyl complexes of acetylenes mediated by (R)-2-piperidino-1,1,2-triphenylethanol takes place with very high enantioselectivity (96-99% ee) to afford the S enantiomers of dicobalt hexacarbo

NHC-catalyzed enantioselective C2-functionalization of 3-hydroxychromenonesviaα,β-unsaturated acyl azoliums

A novel synthetic method for enantioselective C2-functionalization of 3-hydroxychromenones promoted by N-heterocyclic carbenesviathe formation of α,β-unsaturated acyl azolium intermediates, which occurs with Coates-Claisen rearrangement is established. This synthetic strategy enabled the rapid assembly of enantiomerically enriched δ-hydroxychromenone-derived esters/amides under mild conditions with good to excellent yields and broad substrate scope.

Micelle-Mediated Trimerization of Ynals to Orthogonally Substituted 4H-Pyrans in Water: Downstream Rearrangement to Bioactive 2,8-dioxabicyclo[3.3.1]nona-3,6-diene Frameworks

An efficient trimerization of ynals to diversely substituted 4H-pyran constructs has been executed in water, under ambient conditions employing micellar catalysis. The method is in agreement with the ideas of green and sustainable chemistry. The locus of the micellar reaction site has been probed through proton NMR studies. A general acid-mediated downstream rearrangement of the derived 4H-pyrans to interesting 2,8-dioxabicyclo[3.3.1]nona-3,6-dienes has been observed.

Synthesis of Chiral Propargylamines, Chiral 1,2-Dihydronaphtho[2,1-b]furans and Naphtho[2,1-b]furans with C-Alkynyl N,N′-di-(tert-butoxycarbonyl)-aminals and β-Naphthols

Chiral phosphoric acid-catalyzed couplings of C-alkynyl N,N′-di-(tert-butoxycarbonyl)-aminals with β-naphthols led to chiral propargylamines in moderate to high yields with high to excellent enantioselectivity, in which the reactions underwent sequential chiral phosphoric acid-catalyzed in situ formation of N-(tert-butoxycarbonyl)-imines (N-Boc-imines) from the aminals, and 1,2-addition of β-naphthols to the N-Boc-imines. Chiral 1,2-dihydronaphtho[2,1-b]furans and naphtho[2,1-b]furans were prepared with satisfactory results when 10 mol% AgOAc and 20 mol% 2,6-lutidine or 1.2 equiv. of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) were added to the resulting chiral propargylamines solution, respectively.

Transition-metal-free and facile synthesis of 3-alkynylpyrrole-2,4-dicarboxylates from methylene isocyanides and propiolaldehyde

A transition-metal-free, facile and efficient method for the synthesis of 3-alkynylpyrrole-2,4-dicarboxylates from methylene isocyanides and propiolaldehyde with moderate to good yields has been developed. The direct transformation process and good tolerance of various substituents make it an alternative approach to previous protocols, and potential applications of these investigated compounds are expected with or without post-modifications.

Gold-Catalyzed Synthesis of 2,5-Disubstituted Oxazoles from Carboxamides and Propynals

2,5-Disubstituted oxazoles are synthesized by oxidative gold catalysis. In contrast to a reported procedure that delivers 2,4-disubstituted oxazoles starting from terminal alkynes, a switch in selectivity towards a 2,5-disubstitution is achieved by the use of propynals as starting materials. In the new reaction, the key intermediate is formed by the nucleophilic attack of the carboxamide onto a gold carbenoid, and then condensates with the more electrophilic aldehyde moiety already present in the substrate and not with the ketone that is derived from the oxygen donor. This new cyclization mode introduces a new carbonyl moiety as substituent at the 2,5-disubstituted oxazole, an attractive motive that can be found in bioactive compounds or be used for further derivatizations. (Figure presented.).

Copper-Catalyzed Asymmetric Silylation of Propargyl Dichlorides: Access to Enantioenriched Functionalized Allenylsilanes

A copper-catalyzed silylation of propargyl dichlorides was developed to access chloro-substituted allenylsilanes under mild reaction conditions. Moreover, enantioenriched chloro-substituted allenylsilanes can be synthesized in moderate to high yields and good enantioselectivities with this protocol.

Rhodium-Catalyzed 1,1-Hydroacylation of Thioacyl Carbenes with Alkynyl Aldehydes and Subsequent Cyclization

A rhodium-catalyzed 1,1-hydroacylation of thioacyl carbenes with alkynyl and alkenyl aldehydes and subsequent 6-endo-trig/dig cyclization are realized, giving structurally diverse 4H-thiopyran-4-ones and 2,3-dihydro-4H-thiopyran-4-ones in moderate to good yields. The oxidative addition of Rh(I) to aldehydes is proposed to be the turnover-limiting step. Manipulations of estrones demonstrate the applications of our formal (3 + 3) transannulations in the structural modifications of natural products.

Catalyst-Free Annulation of 2-Pyridylacetates and Ynals with Molecular Oxygen: An Access to 3-Acylated Indolizines

A catalyst and additive-free annulation of 2-pyridylacetates and ynals under molecular oxygen was the first developed, affording 3-acylated indolizines in good to excellent yields. Molecular oxygen was used as the source of the carbonyl oxygen atom in indolizines. This approach was compatible with a wide range of functional groups, and especially it has been successfully extended to unsaturated double bonds and triple bonds, which were difficult to prepare by previous methods in a single step.

Gold-Catalyzed [4 + 1]-Annulation Reactions between 1,4-Diyn-3-ols and Isoxazoles to Construct a Pyrrole Core

This work reports gold-catalyzed [4 + 1]-annulation reactions between 1,4-diyn-3-ols and isoxazoles or benzisoxazoles to yield pyrrole derivatives. The reaction chemoselectivity is controlled by an initial attack of an isoxazole at a less hindered alkyne to form gold carbenes, further inducing a 1,2-migration of a second alkyne group. A broad substrate scope of 1,4-diyn-3-ols, isoxazoles and even benzisoxazoles highlighted the reaction utility.