61201-27-2Relevant academic research and scientific papers
Stereodivergent Palladium- And Rhodium-Catalyzed Intramolecular Addition of Tosylureas to Allenes: Diastereoselective Synthesis of Tetrahydropyrimidinones
Breit, Bernhard,Geissler, Arne G. A.,Riesterer, Jasmin R.
supporting information, p. 9168 - 9172 (2021/12/06)
The intramolecular addition of tosylureas to allenes is highly syn-/anti-diastereoselective when employing a palladium or rhodium-based catalytic system and affords 1,3-cyclic ureas. Under palladium catalysis a range of thermodynamic anti-tetrahydropyrimi
Gold-Catalyzed Tandem Oxidative Coupling Reaction between β-Ketoallenes and Electron-Rich Arenes to 2-Furylmethylarenes
Yasukawa, Naoki,Yamada, Yutaro,Furugen, Chikara,Miki, Yuya,Sajiki, Hironao,Sawama, Yoshinari
supporting information, p. 5891 - 5895 (2021/08/18)
A tandem oxidative coupling reaction of β-ketoallenes and arenes was developed, which leads to the formation of 2-furylmethylarenes using AuCl3 and phenyliodine diacetate. The AuIII salt catalyzed the cyclization of β-ketoallenes to form a 2-furylmethyl gold intermediate, and the subsequent C-H functionalization of arenes proceeded smoothly. During the oxidative coupling, nucleophilic additions occurred at the center and terminal carbon atoms of the allene moiety to form C-O and C-C bonds.
Addition of Chloroprene Grignards to Aromatic Aldehydes: Synthesis of Homoallenyl Alcohols
Geissler, Arne G. A.,Breit, Bernhard
supporting information, p. 2621 - 2625 (2021/04/12)
A general procedure for the one-pot synthesis of racemic homoallenyl alcohols from the corresponding aldehyde and chloroprene-derived Grignards is described. Employing bis[2-dimethylaminoethyl]ether (BDMAEE) as an additive at low temperatures shifts the selectivity of the chloroprene Grignard addition to aldehydes such that it is almost exclusive toward allene formation. In a set of follow-up experiments, simple and more elaborate methods for further derivatization have been demonstrated, allowing quick access to more complex structures.
Synthesis of 4,5-Dihydropyrazoles via Palladium-Catalyzed Cyclization Reactions of β,?3-Unsaturated Hydrazones with Aryl Iodides
Ding, Rongcai,Lu, Rongmei,Fang, Zixuan,Liu, Yanjun,Wang, Shaoyu,Liang, Xiaoxia,Zhang, Cheng,Huang, Tianyi,Hu, Jinxing
supporting information, p. 4561 - 4564 (2019/12/24)
A novel two-component cyclization toward the synthesis of polysubstituted 4,5-dihydropyrazoles was carried out: i.e., cyclization of β,?3-unsaturated hydrazones with aryl iodides catalyzed by Pd(0). The reaction forms new carbon-carbon bonds and carbon-ni
Palladium-Catalyzed Stereoselective Cyclization of in Situ Formed Allenyl Hemiacetals: Synthesis of Rosuvastatin and Pitavastatin
Spreider, Pierre A.,Breit, Bernhard
supporting information, p. 3286 - 3290 (2018/06/11)
A diastereoselective palladium-catalyzed cyclization of allenyl hemiacetals is described. It permits the selective synthesis of 1,3-dioxane derivatives, precursors for syn-configured 1,3-diols which make an appearance in all of the statin representatives. The reaction allows the total synthesis of Rosuvastatin and Pitavastatin in a straightforward fashion.
Rhodium-Catalyzed Diastereoselective Cyclization of Allenyl-Sulfonylcarbamates: A Stereodivergent Approach to 1,3-Aminoalcohol Derivatives
Spreider, Pierre A.,Haydl, Alexander M.,Heinrich, Marc,Breit, Bernhard
supporting information, p. 15569 - 15573 (2016/12/09)
A diastereoselective and stereodivergent rhodium-catalyzed intramolecular coupling of sulfonylcarbamates with terminal allenes is described and it provides selective access to 1,3-aminoalcohol derivatives, scaffolds found in bioactive compounds. The reaction is compatible with a large range of different functional groups, thus furnishing products with high diastereoselectivities and yields. Moreover, multigram scale reactions, as well as the application of suitable product transformations were demonstrated.
Aryl-substituted cyclopropyl acetylenes as sensitive mechanistic probes in the gold-catalyzed hydration of alkynes. comparison to the Ag(I)-, Hg(II)-, and Fe(III)-catalyzed processes
Velegraki, Georgia,Stratakis, Manolis
, p. 8880 - 8884 (2013/09/24)
The gold-catalyzed hydration of 2-phenyl- or 2,2-diphenylcyclopropyl acetylene, sensitive probes to trace the formation of vinyl carbocations, provides exclusively the corresponding cyclopropyl methyl ketones. On the other hand, in the Ag(I)- or Fe(III)-c
Conjugated diene-assisted allylic C-H bond activation: Cationic Rh(I)-catalyzed syntheses of polysubstituted tetrahydropyrroles, tetrahydrofurans, and cyclopentanes from Ene-2-dienes
Li, Qian,Yu, Zhi-Xiang
supporting information; experimental part, p. 4542 - 4543 (2010/06/13)
C-H activation followed by addition to alkenes is challenging in the current C-H activation/functionalization field. We report herein an unprecedented diene-assisted transition-metal-catalyzed activation of allylic C-H bonds and their subsequent insertion
First regio- and enantioselective chromium-catalyzed homoallenylation of aldehydes
Coeffard, Vincent,Aylward, Miriam,Guiry, Patrick J.
supporting information; experimental part, p. 9152 - 9155 (2010/03/03)
Game, set, and match: The first regio- and enantioselective version of the title reaction is described. The chiral catalyst prepared in situ from CrCl 3 and a non-C2-symmetric bis(oxazoline) ligand 1 affords the valuable chiral ss-al
Palladium-catalyzed 1-methylene-2-propenylation reactions of aryl bromides with 3,4-alkadien-1-ols via carbon-carbon bond cleavage for the synthesis of 2-aryl-1,3-butadiene derivatives
Imoto, Junichi,Hayashi, Sayuri,Hirano, Koji,Yorimitsu, Hideki,Oshima, Koichiro
experimental part, p. 393 - 400 (2009/06/28)
A method for the synthesis of 2-aryl-1,3-alkadienes has been developed. Treatment of aryl bromides with 3,4-alkadien-1-ols in the presence of a palladium catalyst results in 1-methylene-2-propenyl group transfer to aryl bromides. Taking advantage of palla
