61771-77-5

Usage

Synthesis Reference(s)

Tetrahedron Letters, 17, p. 2975, 1976 DOI: 10.1016/S0040-4039(01)85504-0

Upstream product

• 57416-39-4 Sodium; 2-ethoxycarbonyl-cyclopent-1-enolate 
• 78-95-5 chloroacetone 
• 40702-70-3 ethyl 2-oxo-cyclopentanecarboxylate potassium salt 
• 598-31-2 1-bromoacetone 
• 4749-28-4 2-nitropropene 
• 611-10-9 2-ethoxycarbonyl-1-cyclopentanone 
• 108-22-5 Isopropenyl acetate 
• 109275-09-4 ethyl 1-(2-acetoxy-2-propen-1-yl)-2-oxocyclopentanecarboxylate 
• 77320-46-8 2-oxo-1-prop-2-ynylcyclopentanecarboxylic acid ethyl ester 
• 41975-67-1 1-allyl-2-oxo-cyclopentanecarboxylic acid ethyl ester 

Downstream Products

• 65898-66-0 bicyclo<3.3.0>octene-4 one-3 carboxylate d'ethyle 
• 65611-74-7 2-Acetyl-3-oxo-cyclohexanecarboxylic acid ethyl ester 
• 65611-73-6 4-Acetyl-3-oxo-cyclohexanecarboxylic acid ethyl ester 
• 1461685-94-8 3-{1-[(2S,3aR,6aR)-3a-({(1S,4S)-5-[4-(trifluoromethyl)pyridin-2-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)octahydropentalen-2-yl]piperidin-4-yl}benzoic acid 
• 1461686-07-6 3-{1-[(2R,3aR,6aR)-3a-({(1S,4S)-5-[4-(trifluoromethyl)pyridin-2-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)octahydropentalen-2-yl]piperidin-4-yl}benzoic acid 
• 1461686-03-2 ethyl 3-(1-((2S,3aR,6aR)-3a-((1S,4S)-5-(4-(trifluoromethyl)pyridin-2-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carbonyl)octahydropentalen-2-yl)piperidin-4-yl)benzoate 

Relevant academic research and scientific papers

RUTHENIUM-CATALYZED SYNTHESIS OF 2-ACETOXYALLYL CARBONATES: A SYNTHON FOR PALLADIUM-CATALYZED 2-ACETOXYALLYLATION OF CARBONUCLEOPHILES

Propargyl carbonates react with acetic acid in the presence of a catalytic amount of bis(η5-cyclooctadienyl)ruthenium/PCy3/maleic anhydride at 80 deg C to give 2-acetoxyallyl carbonates in good yields with excellent regioselectivity.These 2-acetoxyallyl carbonates catalytically react with carbonucleophiles in the presence of tetrakis(triphenylphosphine)palladium to give 2-acetoxyallylated products in good to excellent yields.

Ruthenium-Catalyzed Addition Reaction of Acetic acid to Propargyl Alcohol Derivatives: Reagents for Palladium-Catalyzed 2-Acetoxyallylation of Carbonucleophiles

A bis(η5-cyclooctadienyl)ruthenium/PCy3/maleic anhydride system catalyzes the addition reaction of acetic acid to propargyl alcohol derivatives at 80 deg C to give 2-acetoxyallyl derivatives with high selectivity in high yields.The 2-acetoxyallylcarbonates prepared react with carbonucleophiles in the presence of a catalytic amount of Pd(PPh3)4 to give a series of novel polyfunctional enol esters in good to excellent yields.

Intramolecular Schmidt Reaction of Vinyl Azides with Cyclic Ketones

Cyclic ketones tethered with a vinyl azide group undergo a Schmidt-hydrolysis sequence to give secondary lactams bearing a ketone side chain. Secondary lactams are obtained in a regioselective manner that is not possible in a conventional Schimdt reaction. In addition to the well-documented C-2 nucleophilicity, the N nucleophilicity of vinyl azide disclosed in this work opens a new direction for reaction invention involving vinyl azides.

Formation of Bicyclic Cyclopentenone Derivatives by Robinson-Type Annulation of Cyclic β-Oxoesters Containing a 1,4-Diketone Moiety

Robinson-type cyclopentannulations of cyclic β-oxoesters possessing a 1,4-diketone moiety are accomplished under four different Bronsted basic reaction conditions. Using pyrrolidine/acetic acid in DMSO, an oxohexahydrocyclopenta[ a ]indene (42%) and an N

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Cyclic β-oxo esters are converted with enol acetates in a cerium-catalyzed, oxidative Umpolung reaction to furnish 1,4-diketones with up to 95 % yield. Atmospheric oxygen is the oxidant in this process, which can be regarded as ideal from economic and ecological points of view. Further advantages of this new C-C coupling reaction are its operational simplicity and the application of nontoxic and inexpensive CeCl3·7H2O as precatalyst.

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