Article
Chemistry, Multidisciplinary
Tobias Wagener, Lukas Lueckemeier, Constantin G. Daniliuc, Frank Glorius
Summary: This study successfully demonstrates the synthesis of sought-after, enantioenriched delta-lactams through an interrupted hydrogenation mechanism using oxazolidinone-substituted pyridines and water.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Zi-Qi Yi, Fei Chen, Yan-Mei He, Qing-Hua Fan
Summary: A general asymmetric hydrogenation of isoquinolines catalyzed by chiral cationic ruthenium catalysts has been investigated. Various isoquinoline derivatives were efficiently hydrogenated to give chiral tetrahydroisoquinolines with high enantioselectivity. Preliminary mechanistic studies revealed a stepwise reduction pathway for isoquinolines.
Article
Chemistry, Physical
Zhengyu Han, Gang Liu, Xuanliang Yang, Xiu-Qin Dong, Xumu Zhang
Summary: The study developed an efficient and simple synthetic strategy for obtaining both enantiomers of chiral tetrahydroquinoline derivatives through the adjustment of reaction solvents. Gram-scale asymmetric hydrogenation proceeded well with low-catalyst loading, and a possible reaction process was revealed based on various experiments conducted.
Article
Chemistry, Multidisciplinary
Shu-Xin Zhang, Cong Xu, Niannian Yi, Shan Li, Yan-Mei He, Yu Feng, Qing-Hua Fan
Summary: This study successfully achieved the highly efficient ruthenium-catalyzed enantioselective hydrogenation of 9-phenanthrols by trapping the unstable keto tautomers under mild conditions. The method provides a facile access to chiral 9,10-dihydrophenanthren-9-ols with high yield and enantiomeric excess.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Daniel J. Tindall, Steffen Mader, Alois Kindler, Frank Rominger, A. Stephen K. Hashmi, Thomas Schaub
Summary: Sugar alcohols are important for the food industry and can be produced in large quantities with increased yield and stereoselectivity through a homogeneous system.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Multidisciplinary
Andrej Emanuel Cotman
Summary: Noyori-Ikariya-type ruthenium(II)-catalysts have been used for 25 years in asymmetric transfer hydrogenation for the synthesis of chiral secondary alcohols. Recent progress has been made in understanding the asymmetric reduction of complex ketones, controlling up to four stereocenters in a single transformation. Intriguing multi-chiral molecular architectures can be prepared via ATH for drug discovery.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Review
Chemistry, Organic
Dezheng Xie, Ziyi Chen, Chun-Jiang Wang, Xiu-Qin Dong
Summary: Phosphonates and derivatives with an α-chiral center are important compounds found in natural products, pharmaceuticals, and agrochemicals. The synthesis of these compounds has been the focus of recent research, with advancements in asymmetric catalysis such as hydrogenation, addition reactions, and nucleophilic additions to α,β-unsaturated phosphonates. The continuous development of enantioselective catalytic methods and the future applications of these compounds are also discussed.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Organic
Bram B. C. Peters, Norman Birke, Luca Massaro, Pher G. Andersson
Summary: The catalytic asymmetric hydrogenation of olefins is a powerful method for synthesizing chiral compounds. By using an iridium N,P-complex catalyst, various prochiral unsaturated amides can be efficiently reduced with high enantioselectivities. The attractive features of this method include its application in the synthesis of fenpropidin and the potential use of isomeric mixtures as starting materials.
Article
Chemistry, Multidisciplinary
Eliezer Ortiz, Brian J. Spinello, Yoon Cho, Jessica Wu, Michael J. Krische
Summary: Iodide-bound ruthenium-JOSIPHOS complexes catalyze the redox-neutral C-C coupling of primary alcohols with methylallene or 1,3-butadiene to form anti-crotylation products with high levels of diastereo- and enantioselectivity. This method allows for direct crotylation of primary alcohols in the presence of unprotected secondary alcohols, significantly reducing the number of steps required to synthesize substructures of spirastrellolide B and leucascandrolide A.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Jonathan Barrios-Rivera, Yingjian Xu, Guy J. Clarkson, Martin Wills
Summary: The application of enantiomerically-pure ruthenium(II) catalysts containing N - functionalised TsDPEN ligand to the asymmetric transfer hydrogenation of 15 examples of alpha-heterocyclic acetophenone derivatives is reported, with products of up to 99% ee formed. (C) 2021 Elsevier Ltd. All rights reserved.
Review
Chemistry, Multidisciplinary
Johannes Grosskopf, Thorsten Bach
Summary: Upon irradiation with a suitable chiral catalyst, racemic compounds can be converted into enantiopure compounds through a process called photochemical deracemization. This review comprehensively covers the research and current developments in this field, discussing the reactions and mechanistic details underlying the presented reaction. Photochemical deracemization offers a unique opportunity to directly obtain enantiopure compounds from racemates, and short-lived intermediates play a key role in determining the enantioselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Francisco Gaspar, Guilherme S. Caleffi, Paulo C. T. Costa-Junior, Paulo R. R. Costa
Summary: The Noyori-Ikariya Ru-II complexes were utilized to promote the reduction of C=C/C=O bonds in isoflavones, leading to selective formation of cis-3-phenylchroman-4-ols with different substituents at the 2' position of the B-ring in high yields and excellent enantioselectivities. New synthetic strategies for obtaining enantioenriched isoflavanones and pterocarpans were also demonstrated in this study, showcasing the versatility of the developed method.
Article
Chemistry, Physical
Masa Sterle, Matej Hus, Matic Lozinsek, Anamarija Zega, Andrej Emanuel Cotman
Summary: Stereopure CF3-substituted syn-1,2-diols were synthesized through the reductive dynamic kinetic resolution of corresponding alkyl ketones, yielding products with >95% ee and >87:13 syn/anti ratio. This method provides a rapid access to stereopure bioactive molecules. Moreover, DFT calculations were conducted on three types of Noyori-Ikariya ruthenium catalysts to demonstrate their general ability to control stereoselectivity through hydrogen bond acceptor SO2 region and CH/pi interactions.
Review
Chemistry, Organic
Sudipta Ponra, Bernard Boudet, Phannarath Phansavath, Virginie Ratovelomanana-Vidal
Summary: This review summarizes the recent work on the catalytic asymmetric hydrogenation of prochiral olefins, focusing on the development of new catalytic systems and the extension of these asymmetric reductions to new classes of enamides.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Multidisciplinary
Guanghao Huang, Regis Guillot, Cyrille Kouklovsky, Boris Maryasin, Aurelien de la Torre
Summary: A broadly applicable diastereo- and enantioselective inverse-electron-demand Diels-Alder reaction of 2-pyrones and acyclic enol ethers is reported, leading to the synthesis of bridged bicyclic lactones with high yields and enantioselectivities using a copper(II)-BOX catalytic system. Mechanistic studies suggest a stepwise mechanism, and the synthetic potential of the bridged bicyclic lactones is demonstrated through the enantioselective synthesis of polyfunctional cyclohexenes and cyclohexadienes, as well as a carbasugar unit.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Wenpeng Ma, Jianwei Zhang, Cong Xu, Fei Chen, Yan-Mei He, Qing-Hua Fan
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2016)
Article
Chemistry, Organic
Donghui Guo, Jianwei Zhang, Bei Zhang, Jian Wang
Article
Chemistry, Multidisciplinary
Jianwei Zhang, Martin Simon, Christopher Golz, Manuel Alcarazo
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Multidisciplinary
Pablo Redero, Thierry Hartung, Jianwei Zhang, Leo D. M. Nicholls, Guo Zichen, Martin Simon, Christopher Golz, Manuel Alcarazo
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Multidisciplinary
Jianwei Zhang, Biswanath Das, Oscar Verho, Jan-E Backvall
Summary: Here we describe an electrochemical oxidative palladium-catalyzed carbonylation-carbocyclization reaction for the synthesis of gamma-lactones and spirolactones, exhibiting excellent chemoselectivity. Interestingly, electrocatalysis was found to enhance the reaction rate of the tandem process, leading to a more efficient reaction compared to chemical redox conditions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Jianwei Zhang, Martin Simon, Christopher Golz, Manuel Alcarazo
Summary: An Au-catalyzed protocol for the enantioselective synthesis of molecular architectures containing an internal [5]helicene and two peripheral axial stereogenic elements is described. The diastereoselectivity of the double alkyne hydroarylation sequence is not optimal, but the assembly of the C-2-symmetric isomer often occurs with high enantioselectivity. The absolute configurations of the products were determined by X-ray crystallography.
ISRAEL JOURNAL OF CHEMISTRY
(2023)
