138616-38-3

Upstream product

• 3757-88-8 tributylstannylethynylbenzene 
• 109459-28-1 3-(trifluoromethanesulfonyloxy)-2-cyclohexen-1-one 
• 6738-06-3 phenylethynylmagnesium bromide 
• 504-02-9 1,3-cylohexanedione 
• 4440-01-1 lithium phenylacetylide 
• 5323-87-5 3-Ethoxycyclohex-2-en-1-one 
• 536-74-3 phenylacetylene 
• 88841-83-2 3-(Phenylseleno)-2-cyclohexen-1-one 
• 77708-66-8 3-oxocyclohex-1-en-1-yl 4-methylbenzenesulfonate 
• 930-68-7 cyclohexenone 
• 637-44-5 phenylpropyolic acid 
• 23074-59-1 3-isobutoxycyclohex-2-en-1-one 

Downstream Products

• 1270183-42-0 (R)-3-isobutyl-3-(2-phenylethynyl)cyclohexanone 
• 1270183-44-2 (R)-3-(but-3-enyl)-3-(2-phenylethynyl)cyclohexanone 
• 1613527-32-4 (Z)-N-(3-styrylcyclohex-2-enyl)acetamide 
• 1613527-52-8 N-(5-(phenylethynyl)cyclohexa-1,5-dienyl)acetamide 
• 1412791-42-4 C₂₆H₁₈N₂O 
• 1412791-50-4 C₂₆H₁₈N₂O 

Relevant academic research and scientific papers

Palladium-Catalyzed Decarboxylative Coupling of Alkynyl Carboxylic Acids and Alkenyl Tosylates for the Synthesis of Enynones

A palladium-catalyzed decarboxylative coupling reaction was developed for the synthesis of 3-(1-alkynyl)-2-cyclohexen-1-ones. A variety of alkynyl carboxylic acids were coupled with 3-oxocyclohexenyl tosylates to afford the corresponding enynones in good

Stereoselective synthesis of exocyclic allenes by double hydride reduction of 3-alkynyl-2-cycloalkenones

Exocyclic allene natural products and pharmaceutical agents are rare but interesting compounds: Fucoxanthin, grasshopper ketone, and analogues of prostacyclins, cephalosporins, antithrombic agents and sterol biosynthesis inhibitors are representative. Syntheses of exocyclic allenes commonly rely on extended conjugate additions to e.g., alk-2-en-4-ynones, syn SN2′-like additions to alkynyl oxiranes, and substitution reactions such as electrophilic substitutions of propargylic silanes. We report that the reaction of 3-alkynyl-2-cycloalkenones with 2?equiv of various hydridoaluminates but not hydridoborates proceeds via diastereoselective 1,4-reduction of a vinylogously propargylic intermediate alcoholate to provide exocyclic allenes as major products. Isomeric 3-alkynylcycloalkanols also are observed.

Formation of quaternary stereogenic centers by NHC-Cu-catalyzed asymmetric conjugate addition reactions with Grignard reagents on polyconjugated cyclic enones

The copper-catalyzed conjugate addition of various Grignard reagents to polyconjugated enones (dienone and enynone derivatives) is reported. The catalyst system, composed of copper triflate and an NHC ligand, led to the unusual selective formation of the 1,4-addition products. This reaction allows for the creation of all-carbon chiral quaternary centers with enantiomeric excesses up to 99 %. The remaining unsaturation on the 1,4 adducts give access to valuable synthetic transformations. Copyright

Highly enantioselective and regioselective copper-catalyzed 1,4 addition of grignard reagents to cyclic enynones

In this letter we describe an unusual result in terms of regioselectivity with respect to copper-catalyzed conjugate additions of various Grignard reagents to cyclic enynones. The use of Cu(OTf)2 and NHC ligand L1 as the catalyst combination in CH2Cl2 led to the unique formation of the 1,4 adduct. This selectivity does not follow the general trend previously observed in the literature using extended Michael acceptors. Moreover these reactions allowed for the creation of a quarternary stereogenic center with enantioselectivities up to 97% ee.

Efficient synthesis of conjugated alkynyl cycloalkenones: Pd(PPh 3)4-AgOAccatalyzed direct coupling of 1-alkynes with 3-oxocycloalkenyl triflates

Palladium - silver acetate-catalyzed cross coupling of vinyl triflates and 1-alkynes was investigated. This strategy offered a very straightforward and efficient method for access to conjugated alkynyl cycloalkenones from the conjugated vinyl triflates and 1-alkynes. Moreover, the triflates derived from 1,3-cycloalkadione needed no further purification and could be reacted immediately with 1-alkynes to provide the conjugated alkynyl cycloalkenones in excellent overall yields. Copyright

A copper-free palladium catalyzed cross coupling reaction of vinyl tosylates with terminal acetylenes

A copper-free palladium-catalyzed cross coupling of vinyl tosylate (2) and terminal acetylenes was investigated, affording a convenient and efficient method for construction of an sp-sp2 carbon-carbon bond. The tosylate (2) derived from 1,3-cyc

Carbonyl transposition on organoselenium compounds

Carbonyl conjugated vinylic selenides undergo 1,3 and 1,5-carbonyl transposition sequences through organometallic reagents addition reactions followed by acid hydrolysis.

Iodotrimethylsilane-Promoted 1,4-Addition of Copper Acetylides to α,β-Unsaturated Ketones and Aldehydes

In the presence of iodotrimethylsilane (TMSI) and lithium iodide in tetrahydrofuran, the otherwise unreactive copper acetylides add to enones present as s-trans conformers to provide good yields of the silyl enol ethers of β-acetylido carbonyl compounds.

Two methods for the preparation of 2-cyclohexenones from resin-bound 1,3-cyclohexanedione

The addition of organolithium or Grignard reagents to viny]ogous ester resin 1 followed by mild hydrolysis of product resins 2 provides 3-alkyl-2-cyclohexenones in high purity (>95%). Alternatively, conversion of 1 to vinyl triflate resin 4 followed by palladium-mediated couplings with aryl boronic acids and hydrolysis furnishes 3-ary]-2-cyclohexenones in lower yield, but exceptional purity.

Palladium(II)-Catalyzed Coupling of 2-Carboxyethyl Enol Triflates with Organostannanes

Enol triflates 1-5, derived from the corresponding dicarbonyl compound, were coupled with tin reagents 6-8 using Pd(OAc)2 and PPh3 as the catalyst, at 7 mole percent, in 56-91percent yield.