81842-24-2Relevant academic research and scientific papers
Desymmetrizing Isomerization of Alkene via Thiazolinyl Iminoquinoline Cobalt Catalysis
Liu, Wenbo,Zheng, Yushan,Mao, Yihui,Chen, Jieping,Ren, Xiang,Cheng, Zhaoyang,Lu, Zhan
, p. 1158 - 1163 (2022/02/14)
We report a cobalt-catalyzed desymmetrizing isomerization of exo-cyclic alkenes to generate chiral 1-methylcyclohexene derivatives with good yields and enantioselectivities. A novel chiral thiazolinyl iminoquinoline ligand and its cobalt complex were desi
Simple, chemoselective, catalytic olefin isomerization
Crossley, Steven W. M.,Barabé, Francis,Shenvi, Ryan A.
, p. 16788 - 16791 (2015/01/09)
Catalytic amounts of Co(SaltBu,tBu)Cl and organosilane irreversibly isomerize terminal alkenes by one position. The same catalysts effect cycloisomerization of dienes and retrocycloisomerization of strained rings. Strong Lewis bases like amines and imidazoles, and labile functionalities like epoxides, are tolerated.
Synthesis of cyclopropyl silyl ethers and their facile ring opening by photoinduced electron transfer as key step in radical/radical cationic cascade reactions
Waske, Prashant A.,Mattay, Jochen
, p. 10321 - 10330 (2007/10/03)
Various ring-fused cyclopropyl silyl ethers with an benzylic, olefinic or acetylenic side chain have been synthesized. Upon oxidative photoinduced electron transfer (PET) the cyclopropane ring opens and forms a reactive β-keto radical, which undergoes intramolecular cyclization. In some cases we observed only formation of ring opened non-cyclized products. With olefinic side chain 5-exo-trig mode of cyclization rather than 6-endo-trig mode of cyclization takes place whereas in case of acetylenic side chain we observed 6-endo cyclization.
AuCl3-catalyzed synthesis of highly substituted furans from 2-(1-alkynyl)-2-alken-1-ones
Yao, Tuanli,Zhang, Xiaoxia,Larock, Richard C.
, p. 11164 - 11165 (2007/10/03)
Highly substituted furans have been synthesized by the reaction of 2-(1-alkynyl)-2-alken-1-ones and various nucleophiles under very mild reaction conditions in good to excellent yields. Gold and some other transition metals are efficient catalysts for thi
Reductive cyclization of α-cyclopropylketones with alkynyl- and aryl- tethered substituents
Fagnoni, Maurizio,Schmoldt, Philip,Kirschberg, Thorsten,Mattay, Jochen
, p. 6427 - 6444 (2007/10/03)
Photoinduced electron transfer (PET) reactions of α-cyclopropyl- substituted ketones and triethylamine (TEA) were used to initiate the cyclopropylcarbinyl-homoallyl rearrangement. The intramolecular cyclization reaction onto triple bonds was performed yielding bicyclic and spirocyclic compounds. Furthermore, in some preliminary studies it was shown that even intramolecular aromatic substitutions are feasible.
Iron(III) mediated transformations of trimethylsilyloxy cyclopropyl ethers. Part 2: A new 4-substituted-2-cyclohexenone synthesis
Booker-Milburn,Thompson
, p. 12955 - 12962 (2007/10/02)
Conjugate addition of a variety of Grignard reagents to 2-cyclopentenone gave a number of silyl enol ethers (1) which were treated with Et2Zn/CH2I2 to give the corresponding cyclopropyl silyl ethers (2) in good yield. Ferric chloride ring expansion followed by base elimination of the resulting β-chloro ketones gave the 4-substituted-2-cyclohexenones (4) in moderate to good overall yield. The overall process provides a convenient three step route to these enones from 2-cyclopentenone.
A new 4-substituted-2-cyclohexenone synthesis
Booker-Milburn, Kevin I.,Thompson, David F.
, p. 7291 - 7294 (2007/10/02)
Conjugate addition of a variety of Grignard reagents to 2-cyclopentenone followed by cyclopropanation of the resulting enol ethers gave a range of substituted cyclopropyl silyl ethers in good yield. Treatment of these cyclopropyl silyl ethers with ferric chloride in DMF gave the one carbon ring expanded β-chloro ketones which were eliminated to the corresponding 4-substituted-2-cyclohexenones.
ENANTIOSELECTIVE ROUTES TO 2,5-DISUBSTITUTED- AND 4-SUBSTITUTED-2-CYCLOHEXENONES
Asaoka, Morio,Aida, Toshiaki,Sonoda, Syuzo,Takei, Hisashi
, p. 7075 - 7078 (2007/10/02)
Starting with 5-trimethylsilyl-2-cyclohexenone, widely applicable enantioselective routes to the title compounds are established.
Regiocontrolled Synthesis of Mono-, Di, and Trisubstituted Cyclohexenones by Cycloaddition of Vinyl Sulfones to 1-Methoxy-3--1,3-butadienes. Conversion of Alkenes into Effective Dienophilic Reagents
Kinney, William A.,Crouse, Gary D.,Paquette, Leo A.
, p. 4986 - 5000 (2007/10/02)
Cycloaddition of phenyl vinyl sulfone to Danishefky's diene followed by direct ketalization provided 7, a synthon for the 4-(2-cyclohexenyl) anion.Thus, 7 readily undergoes regiospecific γ-alkylation.Ensuing reductive desulfonylation and hydrolysis provides 2-(and 3-)-cyclohexenones efficiently.Zingiberenol, a monocyclic sesquiterpene, was prepared by means of this methodology.Terminal alkenes and cyclic olefins enter into comparable regiocontrolled Diels-Alder addition if they are first subjected to selenosulfonation and oxidation to the vinyl sulfone.Removal of the phenylsulfonyl substituent after condensation provides the adducts which are formally derived from alkylation of the hypothetical C5 anion of 2-cyclohexenone.The scheme can be expanded to include γ-alkylation prior to desulfonylation.By this means, one is able to prepare 4,5-disubstituted 2-(and 3-)cyclohexenones where the nature of the pendant side chains can be widely varied.
A NEW SYNTHON FOR THE REGIOSPECIFIC γ-ALKYLATION OF 2-CYCLOHEXENONES. APPLICATION TO THE SYNTHESIS OF ZINGIBERENOL AND OXYGENATED BICYCLONONANES
Paquette, Leo A.,Kinney, William A.
, p. 131 - 134 (2007/10/02)
The regiospecific γ-alkylation of γ-sulfonylcyclohexenone ketals is described and applied to various synthetic objectives.
