22627-45-8

Upstream product

• 5162-44-7 1-bromo-4-butene 
• 5323-87-5 3-Ethoxycyclohex-2-en-1-one 
• 56671-81-9 3-bromo-2-cyclohexen-1-one 
• 917-57-7 vinyllithium 
• 7103-09-5 4-but-1-enylmagnesium bromide 
• 145102-57-4 ((3-(but-3-en-1-yl)cyclohex-1-en-1-yl)oxy)trimethylsilane 
• 57625-08-8 2-azatricyclo[3.3.1.1^3,7]dec-2-yloxidanyl 
• 1197207-73-0 C₉H₁₄NO⁽¹⁺⁾*NO₃^(1-) 
• 1352617-22-1 1-(azaadamantane-N-oxyl)-1-trimethylsilyloxy-3-(3-butenyl)cyclohex-2-ene 
• 1352617-47-0 C₉H₁₄NO⁽¹⁺⁾*ClO₄^(1-) 
• 1197207-71-8 AZADO+Cl- 
• 930-68-7 cyclohexenone 

Downstream Products

• 121363-31-3 3-(but-3-en-1-yl)-3-methylcyclohexan-1-one 
• 17605-08-2 2-allyl-3-methyl-2-cyclohexen-1-one 
• 84599-68-8 (1R,4R,6R)-Tricyclo[4.4.0.0^1,4]decan-7-one 
• 84599-65-5 (1S,3aR,7aR)-Hexahydro-1,3a-methano-inden-7-one 
• 84599-65-5 (1R,3aS,7aR)-Hexahydro-1,3a-methano-inden-7-one 
• 1097631-09-8 (±)-3-(3-butenyl)-cyclohex-2-en-1-ol 
• 2979-19-3 3,3-dimethylcyclohexanone 
• 1619908-74-5 1,1-dimethyl 2-[2-(3-oxocyclohex-1-enyl)ethyl]cyclopropane-1,1-dicarboxylate 
• 1619908-82-5 C₁₇H₂₄O₅ 
• 1352139-32-2 C₁₈H₂₁NO₃ 
• 121363-32-4 2-((S)-3-But-3-enyl-3-methyl-cyclohexylidene)-[1,3]dithiane 
• 121363-37-9 (S)-3-But-3-enyl-3-methyl-cyclohexanecarboxylic acid methyl ester 
• 121363-33-5 (S)-3-But-3-enyl-3-methyl-cyclohexanecarboxylic acid 
• 121851-32-9 3-(3-Butenyl)-2-(2-naphthalenylthio)-2-cyclohexen-1-one 

Relevant academic research and scientific papers

Oxidative conversion of silyl enol ethers to α,β-unsaturated ketones employing oxoammonium salts

The oxidative conversion of silyl enol ethers to α,β-unsaturated ketones using a less-hindered class of oxoammonium salts (AZADO +BF4-) is described. The reaction proceeds via the ene-like addition of oxoammonium salts to silyl enol ethers.

Formation of quaternary chiral centers by N-Heterocyclic carbene-CuCatalyzed asymmetric conjugate addition reactions with grignard reagents on trisubstituted cyclic enones

The copper-catalyzed conjugate addition of Grignard reagents to 3-substituted cyclic enones allows the formation of all-carbon chiral quaternary centers. We demonstrate in this article that N-heterocyclic carbenes act as efficient chiral ligands for this transformation. High enantioselectivities (up to 96% ee) could be obtained for a variety of substrates.

Stereoselective aziridination of cyclic allylic alcohols using chloramine-T

The stereoselective aziridination of a range of cyclic allylic alcohols using two different chloramine salts (4-MeC6H4SO 2NClNa, TsNClNa and t-BuSO2NClNa, BusNClNa) has been explored. The stereoselectivity of these reactions was highly dependent on the structure of the allylic alcohol and the chloramine salt. Generally, mixtures of cis- and trans-hydroxy aziridines were obtained, in which the major diastereomer was the cis-hydroxy aziridine, whilst complete cis- diastereoselectivity was observed in the aziridination of 1,3-disubstituted allylic alcohols. In each case studied, aziridination using BusNClNa gave higher cis-stereoselectivity than that observed for the same reaction using TsNClNa. Unexpectedly, application of the aziridination conditions to 1-substituted cyclopen-2-en-1-ols did not generate the aziridines. Instead, epoxy sulfonamides were obtained.

Copper-catalyzed asymmetric conjugate addition of trialkylaluminium reagents to trisubstituted enones: Construction of chiral quaternary centers

Me3Al, Et1Al, and vinylalane species undergo enantioselective conjugate addition to a wide range of 2- or 3-substituted enones (cyclopent-2enones, cyclohex-2-enones, 3-methyl cyclohept-2-enone) in the presence of catalytic amount of copper salt (copper thiophene carboxylate, [Cu(CH3-CN)4]BF4 or [CuOTf]2· C6H6) and tropos-phosphoramidite-based ligand. Thus, chiral quaternary centers can be built, with up to 98% ee after rigorous optimization of experimental conditions. It was shown that the main important parameter was the order of the introduction of the reagents. Then, the generated enantioenriched aluminium enolates and the chiral conjugate adducts were functionalized and used for subsequent reactions.

Enantioselective copper-catalyzed conjugate addition to trisubstituted cyclohexenones: Construction of stereogenic quaternary centers

Trimethyl- and triethylaluminum undergo enantioselective conjugate addition to 3-and 2-substituted cyclohexenones in the presence of catalytic amounts of a Cu salt and a phosphoramidite ligand L* (see scheme). Thus, chiral quaternary centers can be built with up to 96.6% ee. Functionalized enones lead to bicyclic structures by a subsequent aldol reaction.

Simple construction of bicyclo[4.3.0]nonane, bicyclo[3.3.0]octane, and related benzo derivatives by palladium-catalyzed cycloalkenylation

(equation presented) Bicyclo[4.3.0]nonanes (hydrindanes) and bicyclo[3.3.0]octanes (octahydropentalenes) are easily synthesized by palladium-catalyzed cycloalkenylations. Additionally, benzo-fused bicyclo[3.3.0]octanes are prepared for the first time thro

Asymmetric spirocyclization: A new type of acid-catalyzed intramolecular 1,4-addition to form carba-spirocyclic compounds

Novel spirocyclization based on intramolecular 1,4-addition and its asymmetric version have been developed using a combination of Lewis acid and 1,2-diol. Treatment of five- and six-membered α,β-unsaturated cyclic ketones having a 4-oxopentyl group at the

Tandem Photocyclization-Intramolecular Addition Reactions of Aryl Vinyl Sulfides. Observation of a Novel Cycloaddition-Allylic Sulfide Rearrangement

Photocyclization of aryl vinyl sulfides reportedly proceeds via thiocarbonyl ylide intermediates.The photochemical behavior of several aryl vinyl sulfides, which incorporate a pendant alkene side chain, was explored.In general, naphthyl and phenyl vinyl thioethers provided products which are consistent with photocyclization to a thiocarbonyl ylide intermediate followed by either intramolecular hydrogen shift or subsequent intramolecular ylide-alkene addition.Product distribution is influenced by solvent and and temperature effects.Novel secondary photoprocesses were also observed during some reactions.Thus, irradiation of naphthyl vinyl sulfide 20 gave dihydrothiophene 22 which underwent subsequent intramolecular cycloaddition to provide 24.Upon prolonged irradiation 24 undergoes a novel allylic sulfide rearrangement to provide 25.

Synthetic Approaches to the Axane Family of Sesquiterpenoids. Total Synthesis of dl-Axamide-4, dl-Axisonitrile-4, and dl-Axisothiocyanate-4

Two methods for the preparation of perhydroindan 7 are described.One involves an intramolecular free radical cyclization in a key step and proceeds in 13 steps and 9percent yield from anisole (9).The other involves an intramolecular conjugate addition med

Stereoselective Synthesis of (+/-)-Indolizidines 167B, 205A, and 207A. Enantioselective Synthesis of (-)-Indolizidine 209B

The first syntheses of the dendrobatid indolizidine alkaloids 167B (3), 205A (4), and 207A (5) are described using as a key step the highly stereoselective intramolecular nitrone cycloaddition of the (Z)-N-alkenylnitrone 10 to prepare the isoxazolidine 11.Mesylate-promoted cyclization of the alcohol 12, followed by reductive cleavage of the resulting mesylate salt, afforded the key axial hydroxymethyl compound 13, which was epimerized via the aldehyde to the equatorial alcohol, and was subsequently reduced to the required 8-methyl-substituted indolizidine.The feasibility of extending this strategy to the enantioselective synthesis of such alkaloids was demonstrated in the first synthesis of (-)-indolizidine 209B (6), whose precursor 10d was obtained from the (S)-glutamate-derived amine 40.