67019-46-9Relevant academic research and scientific papers
Photocatalyzed Transition-Metal-Free Oxidative Cross-Coupling Reactions of Tetraorganoborates**
Music, Arif,Baumann, Andreas N.,Boser, Florian,Müller, Nicolas,Matz, Florian,Jagau, Thomas C.,Didier, Dorian
, p. 4322 - 4326 (2021/02/11)
Readily accessible tetraorganoborate salts undergo selective coupling reactions under blue light irradiation in the presence of catalytic amounts of transition-metal-free acridinium photocatalysts to furnish unsymmetrical biaryls, heterobiaryls and arylated olefins. This represents an interesting conceptual approach to forge C?C bonds between aryl, heteroaryl and alkenyl groups under smooth photochemical conditions. Computational studies were conducted to investigate the mechanism of the transformation.
Electro-Olefination—A Catalyst Free Stereoconvergent Strategy for the Functionalization of Alkenes
Baumann, Andreas N.,Dechent, Jonas,Didier, Dorian,Jagau, Thomas C.,Müller, Nicolas,Music, Arif
, (2020/07/04)
Conventional methods carrying out C(sp2)?C(sp2) bond formations are typically mediated by transition-metal-based catalysts. Herein, we conceptualize a complementary avenue to access such bonds by exploiting the potential of electrochemistry in combination with organoboron chemistry. We demonstrate a transition metal catalyst-free electrocoupling between (hetero)aryls and alkenes through readily available alkenyl-tri(hetero)aryl borate salts (ATBs) in a stereoconvergent fashion. This unprecedented transformation was investigated theoretically and experimentally and led to a library of functionalized alkenes. The concept was then carried further and applied to the synthesis of the natural product pinosylvin and the derivatization of the steroidal dehydroepiandrosterone (DHEA) scaffold.
Enantioselective Synthesis of Chiral Oxime Ethers: Desymmetrization and Dynamic Kinetic Resolution of Substituted Cyclohexanones
Nimmagadda, Sri Krishna,Mallojjala, Sharath Chandra,Woztas, Lukasz,Wheeler, Steven E.,Antilla, Jon C.
, p. 2454 - 2458 (2017/02/23)
Axially chiral cyclohexylidene oxime ethers exhibit unique chirality because of the restricted rotation of C=N. The first catalytic enantioselective synthesis of novel axially chiral cyclohexylidene oximes has been developed by catalytic desymmetrization of 4-substituted cyclohexanones with O-arylhydroxylamines and is catalyzed by a chiral BINOL-derived strontium phosphate with excellent yields and good enantioselectivities. In addition, chiral BINOL-derived phosphoric acid catalyzed dynamic kinetic resolution of α-substituted cyclohexanones has been performed and yields versatile intermediates in high yields and enantioselectivities.
Optimization of TRPV6 calcium channel inhibitors using a 3D ligand-based virtual screening method
Simonin, Céline,Awale, Mahendra,Brand, Michael,Van Deursen, Ruud,Schwartz, Julian,Fine, Michael,Kovacs, Gergely,H?fliger, Pascal,Gyimesi, Gergely,Sithampari, Abilashan,Charles, Roch-Philippe,Hediger, Matthias A.,Reymond, Jean-Louis
, p. 14748 - 14752 (2016/02/05)
Herein, we report the discovery of the first potent and selective inhibitor of TRPV6, a calcium channel overexpressed in breast and prostate cancer, and its use to test the effect of blocking TRPV6-mediated Ca2+-influx on cell growth. The inhib
Catalytic asymmetric hydrogenation of α-arylcyclohexanones and total synthesis of (-)-α-lycorane
Li, Gang,Xie, Jian-Hua,Hou, Jing,Zhu, Shou-Fei,Zhou, Qi-Lin
, p. 1597 - 1604 (2013/07/05)
An efficient catalytic asymmetric hydrogenation of racemic α-arylcyclohexanones with an ethylene ketal group at the 5-position of the cyclohexane ring via dynamic kinetic resolution has been developed, giving chiral α-arylcyclohexanols with two contiguous
Enantioselective baeyer-villiger oxidation: Desymmetrization of meso cyclic ketones and kinetic resolution of racemic 2-arylcyclohexanones
Zhou, Lin,Liu, Xiaohua,Ji, Jie,Zhang, Yuheng,Hu, Xiaolei,Lin, Lili,Feng, Xiaoming
, p. 17023 - 17026,4 (2012/12/12)
Catalytic enantioselective Baeyer-Villiger (BV) oxidations of racemic and meso cyclic ketones were achieved in the presence of chiral N,N'-dioxide-Sc III complex catalysts. The BV oxidations of prochiral cyclohexanones and cyclobutanones afforded series of optically active μ- and γ-lactones, respectively, in up to 99% yield and 95% ee. Meanwhile, the kinetic resolution of racemic 2-arylcyclohexanones was also realized via an abnormal BV oxidation. Enantioenriched 3-aryloxepan-2-ones, whose formation is counter to the migratory aptitude, were obtained preferentially. Both the lactones and the unreacted ketones were obtained with high ee values.
Enantioselective baeyer-villiger oxidation: Desymmetrization of meso cyclic ketones and kinetic resolution of racemic 2-arylcyclohexanones
Zhou, Lin,Liu, Xiaohua,Ji, Jie,Zhang, Yuheng,Hu, Xiaolei,Lin, Lili,Feng, Xiaoming
, p. 17023 - 17026 (2013/01/15)
Catalytic enantioselective Baeyer-Villiger (BV) oxidations of racemic and meso cyclic ketones were achieved in the presence of chiral N,N'-dioxide-Sc III complex catalysts. The BV oxidations of prochiral cyclohexanones and cyclobutanones afforded series of optically active μ- and γ-lactones, respectively, in up to 99% yield and 95% ee. Meanwhile, the kinetic resolution of racemic 2-arylcyclohexanones was also realized via an abnormal BV oxidation. Enantioenriched 3-aryloxepan-2-ones, whose formation is counter to the migratory aptitude, were obtained preferentially. Both the lactones and the unreacted ketones were obtained with high ee values.
Overcoming hERG activity in the discovery of a series of 4-azetidinyl-1-aryl-cyclohexanes as CCR2 antagonists
Zhang, Xuqing,Hufnagel, Heather,Markotan, Thomas,Lanter, James,Cai, Chaozhong,Hou, Cuifen,Singer, Monica,Opas, Evan,McKenney, Sandra,Crysler, Carl,Johnson, Dana,Sui, Zhihua
supporting information; experimental part, p. 5577 - 5582 (2011/10/09)
A series of 4-azetidinyl-1-aryl-cyclohexanes as potent CCR2 antagonists with high selectivity over activity for the hERG potassium channel is discovered through divergent SARs of CCR2 and hERG.
The catalytic asymmetric Fischer indolization
Mueller, Steffen,Webber, Matthew J.,List, Benjamin
supporting information; experimental part, p. 18534 - 18537 (2012/01/31)
The first catalytic asymmetric Fischer indolization is reported. In the presence of a 5 mol % loading of a novel spirocyclic chiral phosphoric acid, 4-substituted cyclohexanone-derived phenylhydrazones undergo a highly enantioselective indolization. Efficient catalyst turnover was achieved by the addition of a weakly acidic cation exchange resin, which removes the generated ammonia. The reaction can be conducted under mild conditions and gives various 3-substituted tetrahydrocarbazoles in generally high yields.
