124931-15-3

Upstream product

• 140-10-3 (E)-3-phenylacrylic acid 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 124931-12-0 diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate 
• 100-52-7 benzaldehyde 
• 102-92-1 Cinnamoyl chloride 
• 66680-87-3 (E)-1-phenyl-(2-tributylstannyl)ethene 
• 30289-28-2 N-methoxy-N-methylcarbamoyl chloride 
• 100-39-0 benzyl bromide 
• 212180-20-6 phenyl(N-methoxy-N-methylcarbamoylmethyl)sulfoxide 
• 100-42-5 styrene 
• 193634-77-4 N-methoxy-N-methylacrylamide 
• 367508-01-8 diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate 
• 1048364-46-0 2-[3,5-bis(trifluoromethyl)phenylsulfonyl]-N-methoxy-N-methylacetamide 
• 217318-54-2 2-diazo-N-methoxy-N-methyl-acetamide 

Downstream Products

• 121712-56-9 (E)-tert-butyl 3,5-dioxo-7-phenylhept-6-enoate 
• 134197-91-4 (1S,3R)-2,2-Dimethyl-3-phenyl-cyclopropanecarboxylic acid methoxy-methyl-amide 
• 1896-62-4 (E)-benzalacetone 
• 14371-10-9 (E)-3-phenylpropenal 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 121712-57-0 (E)-3,5-Dioxo-7-phenyl-hept-6-enoic acid ethyl ester 
• 249306-21-6 ethyl 2-methyl-3,5,7-trioxo-9-phenyl-8-nonenoate 
• 91897-73-3 (1E,4E)-1-phenyl-1,4-hexadien-3-one 
• 930276-98-5 (1E,4E)-1-cyclohexyl-5-phenylpenta-1,4-dien-3-one 
• 115495-48-2 (1E,4E)-1-phenyldeca-1,4-dien-3-one 
• 930277-00-2 (1E,4E)-7-(tert-butyldimethylsilyloxy)-1-phenylhepta-1,4-dien-3-one 
• 25294-56-8 (1E)-6-hydroxy-6-methyl-1-phenyl-1-hepten-4-yn-3-one 
• 1374753-56-6 (R)-N-methoxy-N-methyl-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanamide 
• 300708-87-6 ((E)-2-oxo-4-phenylbut-3-enyl)phosphonic acid dimethyl ester 

Relevant academic research and scientific papers

Regioselective functionalization of pyrones: Facile synthesis of 6-styrylpyrones via KHMDS-mediated aldol condensation

Herein, we disclose our efforts directed toward the synthesis of the kavalactone-based natural product penstyrylpyrone and other related 4-OMe-2-pyrones possessing diverse substituents at the 3-, 5-, and 7-positions. Further, a facile approach to access 6-styrylpyrones via the KHMDS-mediated regioselective aldol condensation of 2-pyrones is described with moderate substrate scope and good to high yields (58–80%). The utility of this methodology was exemplified by the stereoselective construction of desmethoxyyangonin, asnipyrone A, and asnipyrone B.

Assemblies of 1,4-Bis(diarylamino)naphthalenes and Aromatic Amphiphiles: Highly Reducing Photoredox Catalysis in Water

Host-guest assemblies of a designed 1,4-bis(diarylamino)naphthalene and V-shaped aromatic amphiphiles consisting of two pentamethylbenzene moieties bridged by an m -phenylene unit bearing two hydrophilic side chains emerged as highly reducing photoredox catalysis systems in water. An efficient demethoxylative hydrogen transfer of Weinreb amides has been developed. The present supramolecular strategy permits facile tuning of visible-light photoredox catalysis in water.

Selective Construction of C?C and C=C Bonds by Manganese Catalyzed Coupling of Alcohols with Phosphorus Ylides

Herein, we report the manganese catalyzed coupling of alcohols with phosphorus ylides. The selectivity in the coupling of primary alcohols with phosphorus ylides to form carbon-carbon single (C?C) and carbon-carbon double (C=C) bonds can be controlled by the ligands. In the conversion of more challenging secondary alcohols with phosphorus ylides the selectivity towards the formation of C?C vs. C=C bonds can be controlled by the reaction conditions, namely the amount of base. The scope and limitations of the coupling reactions were thoroughly evaluated by the conversion of 21 alcohols and 15 ylides. Notably, compared to existing methods, which are based on precious metal complexes as catalysts, the present catalytic system is based on earth abundant manganese catalysts. The reaction can also be performed in a sequential one-pot reaction generating the phosphorus ylide in situ followed manganese catalyzed C?C and C=C bond formation. Mechanistic studies suggest that the C?C bond was generated via a borrowing hydrogen pathway and the C=C bond formation followed an acceptorless dehydrogenative coupling pathway. (Figure presented.).

CuCl2-catalyzed highly stereoselective and chemoselective reduction of alkynyl amides into α,β-unsaturated amides using silanes as hydrogen donors

A CuH-catalyzed Z-selective partial reduction of alkynyl amides to afford α,β-unsaturated amides using silane as the hydrogen donor is developed. This reaction is carried out under mild conditions and able to accommodate a broad scope of alkynyl amides in

Simple Synthesis of Amides via Their Acid Chlorides in Aqueous TPGS-750-M

The technology of surfactant chemistry is employed for amide bond construction via the reaction of acyl chlorides with amines in 2 wt % TPGS-750-M aqueous solution. Specifically, this highly efficient method enables a chromatography-free scalable process and recycling of the TPGS-750-M solution.

Selective Reduction of α,β-Unsaturated Weinreb Amides in the Presence of α,β-Unsaturated Esters

α,β-Unsaturated esters were selectively protected in situ in the presence of α,β-unsaturated Weinreb amides using PEt3 and trimethylsilyl trifluoromethanesulfonate (TMSOTf) in toluene under reflux. Diisobutylaluminium hydride (DIBAL-H) reduction of the mixture followed by tetra-n-butylammonium fluoride (TBAF) treatment produced α,β-unsaturated aldehydes in good yields along with the recovered α,β-unsaturated esters.

General Method for the Preparation of Indole-2-Weinreb Amides

Indole-2-Weinreb amides are obtained via thermolysis of α-azidocinnamic acid Weinreb amides in a Hemetsberger-Knittel-type cyclization. The required vinyl azides are not accessible by Knoevenagel condensation, but are obtained by cerium(IV)-mediated oxida

Chalcone and cinnamate synthesis via one-pot enol silane formation-Mukaiyama aldol reactions of ketones and acetate esters

Aryl alkyl ketones, acetate esters, and acetamides undergo facile one-pot enol silane formation, Mukaiyama aldol addition, and dehydrosilyloxylation in the presence of an amine base and excess trimethylsilyl trifluoromethanesulfonate. The chalcone and cinnamate products are generally recovered in high yield. The relative stoichiometry of the trimethylsilyl trifluoromethanesulfonate and amine base reagents determines whether the reaction yields the β-silyloxy carbonyl product or the α,β-unsaturated carbonyl.

Stereospecific Decarboxylative Nazarov Cyclization Mediated by Carbon Dioxide for the Preparation of Highly Substituted 2-Cyclopentenones

Highly substituted 2-cyclopentenones were stereospecifically and regioselectively constructed with high catalytic efficiency through Lewis-acid catalyzed decarboxylative Nazarov cyclization of the cyclic carbonate derivative, which is prepared by reacting the propargyl alcohol with carbon dioxide in the presence of a silver catalyst. The stereochemistry of the 2-cyclopentenone is strictly controlled by the geometry of the alkene in the starting material. This method is applicable for various substrates.

Synthesis of Difluoromethyl Ketones from Weinreb Amides, and Tandem Addition/Cyclization of o-Alkynylaryl Weinreb Amides

[Difluoro(phenylsulfanyl)methyl]trimethylsilane (PhSCF2SiMe3) underwent a fluoride-induced nucleophilic addition to the carbonyl group of Weinreb amides to provide the corresponding difluoro(phenylsulfanyl)methyl ketones. These were