924906-61-6

Upstream product

• 100-46-9 benzylamine 
• 37614-59-8 4-(4-methoxyphenyl)prop-2-yn-1-ol 
• 924906-80-9 Methanesulfonic acid 3-(4-methoxy-phenyl)-prop-2-ynyl ester 

Downstream Products

• 924906-85-4 N-benzyl-N-(3-(4-methoxyphenyl)prop-2-ynyl)-2,2-dimethylhexa-3,4-dienamide 
• 1373169-45-9 (1-benzyl-2-phenyl-1H-imidazol-4-yl)(4-methoxyphenyl)methanone 
• 1373169-41-5 N-benzyl-N-(3-(4-methoxyphenyl)prop-2-yn-1-yl)benzimidamide 

Relevant academic research and scientific papers

Palladium-Catalyzed Carbo-Oxygenation of Propargylic Amines using in Situ Tether Formation

1,2-Amino alcohols and α-aminocarbonyls are frequently found in natural products, drugs, chiral auxiliaries, and catalysts. This work reports a new method for the palladium-catalyzed oxyalkynylation and oxyarylation of propargylic amines. The reaction is perfectly regioselective based on the in situ introduction of a hemiacetal tether derived from trifluoroacetaldehyde. cis-Selective carbo-oxygenation was achieved for terminal alkynes, whereas internal alkynes gave trans-carbo-oxygenation products. The obtained enol ethers could be easily transformed into 1,2-amino alcohols or α-amino ketones using hydrogenation or hydrolysis, respectively.

Enantioselective Carboetherification/Hydrogenation for the Synthesis of Amino Alcohols via a Catalytically Formed Chiral Auxiliary

Chiral auxiliaries and asymmetric catalysis are the workhorses of enantioselective transformations, but they still remain limited in terms of either efficiency or generality. Herein, we present an alternative strategy for controlling the stereoselectivity of chemical reactions. Asymmetric catalysis is used to install a transient chiral auxiliary starting from achiral precursors, which then directs diastereoselective reactions. We apply this strategy to a palladium-catalyzed carboetherification/hydrogenation sequence on propargylic amines, providing fast access to enantioenriched chiral amino alcohols, important building blocks for medicinal chemistry and drug discovery. All stereoisomers of the product could be accessed by the choice of ligand and substituent on the propargylic amine, leading to a stereodivergent process.

Palladium-Catalyzed Carboxy-Alkynylation of Propargylic Amines Using Carbonate Salts as Carbon Dioxide Source

A palladium-catalyzed multicomponent reaction of propargylic amines, alkynyl bromides and cesium hydrogen carbonate to access oxazolidinones is reported. In contrast to previous reports, only a slight excess of cesium hydrogen carbonate is used as a surrogate of carbon dioxide. The reaction gives access to oxazolidinones bearing alkyl- and aryl polysubstituted enynes in good yield and very high E stereoselectivity.

Rhodium(I)-catalyzed allenic carbocyclization reaction affording δ- and ε-lactams

(Chemical Equation Presented) This letter extends the scope of the rhodium(I)-catalyzed allenic Alder-ene carbocyclization reaction to the preparation of δ- and ε-lactams from amides. A variety of allenic propiolamides were cycloisomerized to give a numbe