72137-22-5Relevant academic research and scientific papers
Hydroboration. 76. Hydroboration of Cyclic Dienes with Representative Hydroborating Agents
Brown, Herbert C.,Bhat, Krishna S.
, p. 445 - 449 (1986)
A detailed study was made of the hydroboration of cyclic dienes with representative hydroborating agents: borane-methyl sulfide (BMS), 9-borabicyclononane (9-BBN), disiamylborane (Sia2BH), dibromo-borane-methyl sulfide (Br2BH*SMe2), and dibromoborane (Br2BH). 1,4-Cyclohexadiene essentially undergoes monohydroboration with a stoichiometric amount of the representative hydroborating agents, whereas 1,5-cyclooctadiene gives the dihydroboration product predominantly.The rapid dimerization of 1,3-cyclopentadiene introduces a complication into its hydroboration.However, monomeric cyclopentadiene undergoes hydroboration primarily to the homoallylic derivative with little of the desired allylic product.Hydroboration of 1,3-cyclohexadiene with a stoichiometric amount of the hydroborating agent furnishes mainly the allylboranes, which upon treatment with acetaldehyde followed by oxidation, furnishes 1-(2-cyclohexenyl)-1-ethanol in good yield.Similary, hydroboration of 1,3-cycloheptadiene and 1,3-cyclooctadiene furnished dihydroborated products preferentially, with lower yields of the corresponding allylboranes, characterized as 1-(2-cycloheptenyl)-1-ethanol and 1-(2-cyclooctenyl)-1-ethanol, respectively, following reaction with acetaldehyde.
A practical and scaleable synthesis of 1r,5s-bicyclo[3.1.0]hexan-2-one: The development of a catalytic lithium 2,2,6,6-tetramethylpiperidide (LTMP) mediated intramolecular cyclopropanation of (R)-1,2-epoxyhex-5-ene
Alorati, Anthony D.,Bio, Matthew M.,Brands, Karel M. J.,Cleator, Ed,Davies, Antony J.,Wilson, Robert D.,Wise, Chris S.
, p. 637 - 641 (2007)
An efficient synthesis of 1R,5S-bicyclo[3.1.0]hexan-2-one from (R)-1,2-epoxyhex-5-ene is described. Development of a catalytic intramolecular cyclopropanation of (R)-1,2-epoxyhex-5-ene gives the key homochiral bicycle[3.1.0]hexan-1-ol, which is then oxidized to the desired ketone. This process has been successfully demonstrated on a multi-kilogram scale.
Stereoselective Synthesis of 7-(E)-Arylidene-2-chloro-6-azabicyclo[3.2.1]octanes via Aluminum Chloride-Promoted Cyclization/Chlorination of Six-Membered Ring 3-Enynamides
Yeh, Ming-Chang P.,Chang, Yi-Mei,Lin, Hsin-Hui
, p. 2196 - 2201 (2017)
An efficient stereoselective synthesis of 7-(E)-arylidene-2-chloro-6-azabicyclo[3.2.1]octanes is described. The aluminum chloride-promoted cyclization/chlorination of six-membered ring 3-enynamides enables a straightforward approach to the 6-azabicyclo[3.2.1]octane nucleus that is incorporated in many biologically active compounds. Acid treatment of the resultant chlorinated arylideneazabicyclooctanes furnishes 3-alkanoyl-4-chlorocyclohexanamines in excellent yields and high stereoselectivity. (Figure presented.).
Tuning acylthiourea ligands in Ru(II) catalysts for altering the reactivity and chemoselectivity of transfer hydrogenation reactions, and synthesis of 3-isopropoxy-1H-indole through a new synthetic approach
Sathishkumar, Pushpanathan N.,Prabha, Padinhattath Sachind,Bhuvanesh, Nattamai S.P.,Karvembu, Ramasamy
, (2020/01/09)
Ru(II)-p-cymene complexes (1–3) containing picolyl based pseudo-acylthiourea ligands (L1-L3) were synthesized and characterized. The crystallographic study confirmed the molecular structures of all the ligands (L1-L3) and complex 3. The catalytic activity of the complexes was tested mainly towards TH of carbonyl compounds and nitroarenes. The influence of steric and electronic effects of the ligands on the chemoselectivity and reactivity were reported. The catalytic activity was enhanced and chemoselectivity was switched after tuning the ligands in the catalysts, compared to their corresponding unmodified Ru(II)-p-cymene complexes. The catalysis was extended to a broad range of substrates including some challenging systems like furfural, benzoylpyridine, benzoquinone, chromanone, etc. The strategy of tuning the bifunctional ligands in the catalysts for effective and selective catalysis worked nicely. Further, the catalysis was extended to one pot synthesis of 3-isopropoxyindole from 2-nitrocinnamaldehyde, the first synthetic route similar to Baeyer Emmerling indole synthesis. All the catalytic experiments exhibited high conversion and selectivity.
Photoredox/Cobalt Dual-Catalyzed Decarboxylative Elimination of Carboxylic Acids: Development and Mechanistic Insight
Cartwright, Kaitie C.,Joseph, Ebbin,Comadoll, Chelsea G.,Tunge, Jon A.
, p. 12454 - 12471 (2020/09/09)
Recently, dual-catalytic strategies towards the decarboxylative elimination of carboxylic acids have gained attention. Our lab previously reported a photoredox/cobaloxime dual catalytic method that allows the synthesis of enamides and enecarbamates directly from N-acyl amino acids and avoids the use of any stoichiometric reagents. Further development, detailed herein, has improved upon this transformation's utility and further experimentation has provided new insights into the reaction mechanism. These new developments and insights are anticipated to aid in the expansion of photoredox/cobalt dual-catalytic systems.
Ru-Photoredox-Catalyzed Decarboxylative Oxygenation of Aliphatic Carboxylic Acids through N-(acyloxy)phthalimide
Zheng, Chao,Wang, Yuting,Xu, Yangrui,Chen, Zhen,Chen, Guangying,Liang, Steven H.
, p. 4824 - 4827 (2018/08/24)
Decarboxylative aminoxylation of aliphatic carboxylic acid derivatives with (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO) in the presence of ruthenium photoredox catalysis is reported. The key transformation entails a highly efficient photoredox catalytic cycle using Hantzsch ester as a reductant. The ensuing alkoxyamine can be readily converted to the corresponding alcohol in one pot, representing an alternative approach to access aliphatic alcohols under photoredox conditions.
Construction of bicyclic systems containing an oxygen bridge by isomerization of cyclic epoxy alcohols
Iwakura, Masaru,Tokura, Hiroshi,Tanino, Keiji
supporting information, p. 1223 - 1226 (2017/03/02)
A novel method for constructing a 7-oxabicyclo[2.2.1]heptane skeleton was developed. The substrates, namely cis-3,4-epoxy-1-cyclohexanol derivatives, were prepared from the corresponding 3-cyclohexen-1-ol derivatives via a stereoselective epoxidation reaction using a vanadium catalyst. Upon heating with lithium iodide in propionitrile, the cis-epoxy alcohol was transformed into the 7-oxabicyclo[2.2.1]heptane derivative in high yield. The reaction proceeds through formation of a lithium alkoxide bearing an iodohydrin moiety, followed by an intramolecular SN2 reaction.
Highly Enantioselective Construction of Hajos-Wiechert Ketone Skeletons via an Organocatalytic Vinylogous Michael/Stetter Relay Sequence
Jia, Zhi-Long,Wang, Yao,Zhao, Chuan-Gang,Zhang, Xiao-Hai,Xu, Peng-Fei
supporting information, p. 2130 - 2133 (2017/04/27)
A highly enantioselective supramolecular iminium-catalyzed vinylogous Michael addition/Stetter relay sequence has been developed. This transformation provided a series of Hajos-Wiechert-type fused bicyclic diones with three continuous stereogenic centers in good yields with excellent enantioselectivities. The obtained products can be easily transformed into other structures with potential synthetic value.
SULFIDE ALKYL COMPOUNDS FOR HBV TREATMENT
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Paragraph 0505, (2016/06/28)
The present invention includes a method of inhibiting, suppressing or preventing HBV infection in an individual in need thereof, comprising administering to the individual a therapeutically effective amount of at least one compound of the invention.
A homogeneous gallium(III) compound selectively catalyzes the epoxidation of alkenes
Jiang, Wenchan,Gorden, John D.,Goldsmith, Christian R.
body text, p. 2725 - 2727 (2012/04/23)
We demonstrate that a simple gallium(III) complex, [Ga(phen) 2Cl2]Cl (phen = 1,10-phenanthroline), can serve as a homogeneous catalyst for the epoxidation of alkenes. The olefin epoxidations proceed relatively quickly at mild temperatures and, under optimum conditions, are highly selective for the epoxide product.
