106318-93-8

Upstream product

• 2579-22-8 Phenylpropargyl aldehyde 
• 104-94-9 4-methoxy-aniline 

Downstream Products

• 159051-06-6 3,3-Bis-ethylsulfanyl-1-(4-methoxy-phenyl)-4-phenylethynyl-azetidin-2-one 
• 173095-49-3 (3S,4R,5S)-4-ethoxycarbonyl-3-hydroxy-1-(4-methoxyphenyl)-5-phenylpropargyl-2-pyrrolidinone 
• 929611-60-9 C₂₆H₂₉NO₄ 
• 929611-67-6 C₂₇H₃₁NO₄ 
• 929611-74-5 C₂₃H₂₂N₂O₂ 
• 929611-61-0 C₂₄H₂₅NO₄ 
• 929611-63-2 C₂₅H₂₇NO₄ 
• 929611-71-2 C₂₂H₂₀N₂O₂ 

Relevant academic research and scientific papers

Development of a syn-Selective Mannich Reaction of Aldehydes with Propargylic Imines by Dual Catalysis: Asymmetric Synthesis of Functionalized Propargylic Amines

Direct coupling of enolizable aldehydes with C-alkynyl imines is realized affording the corresponding propargylic Mannich adducts of syn configuration, thus complementing previous methods that gave access to the anti-isomers. The combination of proline and a urea Br?nsted base cocatalyst is key for the reactions to proceed under very mild conditions (3-10 mol % catalyst loading, dichloromethane as solvent, -20 °C, 1.2 molar equivalents of aldehyde) and with virtually total stereocontrol (syn/anti ratio up to 99:1; ee up to 99 %). Some possibilities of further chemical elaboration of adducts are also briefly illustrated.

Prolinate Salt as a Catalyst in the syn -Selective, Asymmetric Mannich Reaction of Alkynyl Imine

Prolinate salt is an efficient catalyst in the Mannich reaction of alkynyl imine and aldehyde, to afford synthetically useful chiral propargyl amine derivatives with excellent syn-selectivity and nearly perfect control of the absolute configuration. The c

Asymmetric Petasis Borono-Mannich Allylation Reactions Catalyzed by Chiral Biphenols

Chiral biphenols catalyze the asymmetric Petasis borono-Mannich allylation of aldehydes and amines through the use of a bench-stable allyldioxaborolane. The reaction proceeds via a two-step, one-pot process and requires 2–8 mole % of 3,3′-Ph2-BINOL as the optimal catalyst. Under microwave heating the reaction affords chiral homoallylic amines in excellent yields (up to 99 %) and high enantioselectivies (er up to 99:1). The catalytic reaction is a true multicomponent condensation reaction whereas both the aldehyde and the amine can possess a wide range of structural and electronic properties. Use of crotyldioxaborolane in the reaction results in stereodivergent products with anti- and syn-diastereomers both in good diastereoselectivities and enantioselectivities from the corresponding E- and Z-borolane stereoisomers.

An efficient one-pot synthesis of 1,4-disubstituted 3-amino-2-pyridone derivatives via three-component reactions of alkynyl aldehydes and amines with ethyl 2-((diphenylmethylene)amino)acetate

A facile and efficient one-pot synthesis of 1,4-disubstituted 3-amino-2-pyridone derivatives via three-component reactions of readily available alkynyl aldehydes, amines, and ethyl 2-((diphenylmethylene)amino) acetate has been developed. The alkynyl aldeh

Novel 2-pyridone synthesis via nucleophilic addition of malonic esters to alkynyl imines

(Matrix presented) A novel 2-pyridone synthesis via nucleophilic addition of malonic esters to alkynyl imines has been developed. The reaction of dialkylalkyl sodiomalonates with alkynyl imines provided 2-pyridones in good to excellent yields.

Application of erythro-2-amino-1,2-diphenylethanol as a highly efficient chiral auxiliary. highly stereoselective staudinger-type β-lactam synthesis using a 2-chloro-l-methylpyridinium salt as the dehydrating agent

The Staudinger-type reaction of carboxylic acids with imines, using a 2-chloro-l-methylpyridinium salt as the dehydrating reagent, proceeded smoothly under mild conditions to afford the desired β-lactams in high yields with excellent cis-selectivity. This

Stereoselectivity in the Condensation Reactions between Malate Enolate and Imines to 2-Pyrrolidinone Derivatives

Enolate dianion of diethyl (S)-malate was stereoselectively condensed with nonenolizable N-arylimines to give 2-pyrrolidinone derivatives.The presence of HMPA changes the diastereoselectivity of this cyclization reaction.

Synthesis of novel β-lactam core structures related to the penam and penem antibiotics

The synthesis of a structurally new class of penicillin- and penem-type ring systems is described which is based on a sequential imine-ketene cycloaddition reaction and halogen-induced sulfide cyclization process.

Reaction of Reissert Anion with Aldimines: A New Approach to the Imidazoisoquinoline Ring System

The carbanion derived from N-alkoxycarbonyl Reissert compound readily undergoes addition-cyclization reaction with aldimines to give imidazoisoquinolines.A detailed study of this new ring annelation chemistry is described.

The synthesis of 3-carboxymethyleneazetidinones

A series of novel azetidinones bearing the methoxycarbonylmethylene, thioethoxycarbonylmethylene, and alkylaminocarbonylmethylene side chain in their three position have been synthesized from the reaction of the potassium salt of 4,4'-bis(thioethoxy)-3-bu