Review
Chemistry, Inorganic & Nuclear
Jessica Margalef, Maria Biosca, Pol de la Cruz Sanchez, Jorge Faiges, Oscar Pamies, Montserrat Dieguez
Summary: The success of phosphine-oxazoline ligands has led to advancements in P-oxazoline ligand families, resulting in diverse structures and more efficient ligands for asymmetric transformations. Through proper design, these heterodonor bidentate ligand families exhibit superior catalytic performance in a variety of asymmetric reactions.
COORDINATION CHEMISTRY REVIEWS
(2021)
Article
Chemistry, Applied
Yin-Feng Ma, Chuan-Jin Hou, De-Quan Wei, Xinwei He, Ting-Ting Chu, Xiu-shuai Chen, Xiang-Ping Hu
Summary: The asymmetric hydrogenation of beta-ketophosphonates with chiral Ir/P,N,N-ligands catalyst leads to high yields of beta-hydroxyphosphonates with good or excellent enantioselectivities under mild conditions.
APPLIED ORGANOMETALLIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Wei Zhao, Wenji Wang, Huan Zhou, Qishan Liu, Zhiqing Ma, Haizhou Huang, Mingxin Chang
Summary: A one-pot asymmetric hydrogenation of pyridines with subsequent N-alkylation using a traceless Bronsted acid activation strategy is reported. The reaction exhibits high stereoselectivity and can be used to synthesize indolizidines and quinolizidines. Experimental and theoretical studies reveal that chloride anion and noncovalent interactions play important roles in determining the stereoselectivity of the reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(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, Applied
Maria Biosca, Pol de la Cruz-Sanchez, Daniel Tarr, Patricia Llanes, Erik A. Karlsson, Jessica Margalef, Oscar Pamies, Miquel A. Pericas, Montserrat Dieguez
Summary: A chiral phosphine-triazole ligand has been developed for the Ir-catalyzed asymmetric hydrogenation of exocyclic benzofused alkenes, which overcomes previous limitations and exhibits excellent enantioselectivity. The catalyst shows good tolerance towards various substituents and substitution patterns at both aromatic rings, making it an effective tool for hydrogenation of exocyclic olefins.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Pep Rojo, Agusti Lledos, Antoni Riera, Xavier Verdaguer
Summary: A threonine-derived phosphine-oxazoline iridium catalyst with excellent selectivity in the hydrogenation of N-Boc-2,3-diarylallylamines is reported. The reversible cyclometallation process and the influence of substitution at the phenyl group of the oxazoline on this equilibrium are thoroughly investigated. X-Ray analysis reveals the coordination mode of the cyclometallated tridentate ligand. Furthermore, the utilization of Ir(III) pre-catalysts or Ir(I)/Ir(III) mixtures in hydrogenation reactions is proposed based on the observed equilibrium dynamics.
Article
Chemistry, Multidisciplinary
Yongjia Shi, Yuhuan Yang, Senmiao Xu
Summary: This study presents the first example of transition-metal-catalyzed regio- and stereo-controllable C-H functionalization, achieving a broad range of functional groups and high enantioselectivities.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Maria Biosca, Pol de la Cruz-Sanchez, Jorge Faiges, Jessica Margalef, Ernest Salomo, Antoni Riera, Xavier Verdaguer, Joan Ferre, Feliu Maseras, Maria Besora, Oscar Pamies, Montserrat Dieguez
Summary: Ir-MaxPHOX-type catalysts exhibit high catalytic performance in the hydrogenation of a wide range of nonchelating olefins with different geometries, substitution patterns, and degrees of functionalization. These air-stable and readily available catalysts have been successfully used in the asymmetric hydrogenation of di-, tri-, and tetrasubstituted olefins (ee ' s up to 9996). The combination of theoretical calculations and deuterium labeling experiments has revealed the factors responsible for the observed enantioselectivity, allowing for the rationalization of suitable substrates for these Ircatalysts.
Article
Chemistry, Multidisciplinary
Si-Yong Yin, Qiansujia Zhou, Chen-Xu Liu, Qing Gu, Shu-Li You
Summary: The iridium-catalyzed asymmetric C-H alkylation was used for the first time to construct N-N biaryl atropisomers. The method showed good yields (up to 98%) and excellent enantioselectivity (up to 99% ee) for the synthesis of axially chiral molecules based on indole-pyrrole skeleton. This method also allowed the synthesis of N-N bispyrrole atropisomers with high yields and enantioselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Inorganic & Nuclear
Lakshay Kathuria, Ashoka G. Samuelson
Summary: The enantioselective reduction of imines to chiral secondary amines was studied using chiral half-sandwich iridium complexes with N-heterocyclic carbene ligands. The optimized conditions showed good yields for ketimines with moderate enantiomeric excess. The Ir complex with phenylglycine-derived chiral NHC exhibited the highest catalytic activity and enantiomeric excess compared to other NHCs in the series.
Article
Chemistry, Organic
Dominik Albat, Alicia Koecher, Julia Witt, Hans-Guenther Schmalz
Summary: This study identified a new superior ligand (L24*) through screening a set of chiral phosphoramidites, which enabled the synthesis of amination products with high enantioselectivity under optimized conditions. This ligand also exhibited outstanding diastereoselectivity and negligible matched/mismatched differences in the N-allylation of other amino acid tert-butyl esters.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Lin Liu, Kai-Xin Guo, Yu Tian, Chang-Jiang Yang, Qiang-Shuai Gu, Zhong-Liang Li, Liu Ye, Xin-Yuan Liu
Summary: The copper-catalyzed asymmetric cross-coupling of C(sp(3))-C(sp) bonds with terminal alkynes reported in this study shows high to excellent enantioselectivity. The rational design of chiral oxazoline-derived ligands is critical for success in tolerating oxidative conditions and inducing challenging enantiocontrol. This approach offers direct access to a variety of synthetically useful compounds and has great potential for the synthesis of enantioenriched medicinally relevant compounds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Yu-Qing Bai, Xin-Wei Wang, Bo Wu, Xiao-Qing Wang, Rong-Zheng Liao, Man Li, Yong-Gui Zhou
Summary: The development of chiral ligands for precise stereocontrol is essential in asymmetric catalysis. However, the utilization of chiral oxazole-pyridine-type ligands has been limited compared to established chiral pyridine-pyridine and pyridine-oxazoline-type ligands. In this study, a new class of planar-chiral oxazole-pyridine N,N-ligands based on [2.2]paracyclophane was designed and synthesized. These ligands exhibited excellent performance in the enantioselective palladium-catalyzed acetoxylative cyclization, providing chiral cis-hydrobenzofurans with potent NF-κB inhibition, thereby demonstrating the promising potential of chiral oxazole-pyridine ligands as an efficient N,N-ligand scaffold.
Article
Chemistry, Multidisciplinary
Jose A. Carmona, Patricia Rodriguez-Salamanca, Rosario Fernandez, Jose M. Lassaletta, Valentin Hornillos
Summary: An atroposelective Ir-catalyzed dynamic kinetic resolution (DKR) of 2-(quinolin-8-yl)benzaldehydes/1-naphthaldehydes is achieved by transfer hydrogenative coupling of allyl acetate. The reaction leads to the installation of central and axial chirality, with high diastereoselectivities and excellent enantioselectivities when ortho-cyclometalated iridium-DM-BINAP is used as the catalyst. The racemization of the substrates is facilitated through a designed transient Lewis acid-base interaction between the quinoline nitrogen atom and the aldehyde carbonyl group.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Conor L. Oates, Alister S. Goodfellow, Michael Buhl, Matthew L. Clarke
Summary: DFT calculations were carried out on the full catalytic cycle of manganese catalysed enantioselective hydrogenation of a selection of ketones. It was found that Mn complexes with a chiral P,N,N ligand showed the highest reactivity in a facial coordination mode. The use of a new ligand transformed the levels of enantioselectivity for the hydrogenation of cyclic ketones. In silico evaluation of substrates accurately predicted experimental results.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Rene Tannert, Marina Schwan, Lorenz Ratke
JOURNAL OF SUPERCRITICAL FLUIDS
(2015)
Article
Chemistry, Applied
Martin Wickenheisser, Annika Herbst, Rene Tannert, Barbara Milow, Christoph Janiak
MICROPOROUS AND MESOPOROUS MATERIALS
(2015)
Article
Chemistry, Physical
Marina Schwan, Rene Tannert, Lorenz Ratke
JOURNAL OF SUPERCRITICAL FLUIDS
(2016)
Article
Materials Science, Ceramics
Rene Tannert, Marina Schwan, Ameya Rege, Mario Eggeler, Julio Cesar da Silva, Marion Bartsch, Barbara Milow, Mikhail Itskov, Lorenz Ratke
JOURNAL OF SOL-GEL SCIENCE AND TECHNOLOGY
(2017)
Article
Chemistry, Multidisciplinary
Herbert Waldmann, Tai-Shan Hu, Steffen Renner, Sascha Menninger, Rene Tannert, Toshiro Oda, Hans-Dieter Arndt
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2008)
Article
Chemistry, Multidisciplinary
Rene Tannert, Tai-Shan Hu, Hans-Dieter Arndt, Herbert Waldmann
CHEMICAL COMMUNICATIONS
(2009)
Article
Chemistry, Multidisciplinary
Igor D. Jurberg, Indranil Chatterjee, Rene Tannert, Paolo Melchiorre
CHEMICAL COMMUNICATIONS
(2013)
Article
Chemistry, Multidisciplinary
Rene Tannert, Lech-Gustav Milroy, Bernhard Ellinger, Tai-Shan Hu, Hans-Dieter Arndt, Herbert Waldmann
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2010)
Article
Polymer Science
Fabian Henn, Rene Tannert
Summary: In materials research, controlling the wettability of surfaces is crucial for various applications. This study presents a method to modify the wettability of monolithic xerogels by silation. The resulting hydrophobic gels demonstrated excellent wetting behavior over an extended period of time. This research provides insights into the functionalization of phenolic-based gels, highlighting the potential for their applications in diverse fields.
Article
Crystallography
Rene Tannert, Markus Schuermann, Hans Preut, Hans-Dieter Arndt, Herbert Waldmann
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE
(2007)
Article
Chemistry, Multidisciplinary
Tai-Shan Hu, Rene Tannert, Hans-Dieter Arndt, Herbert Waldmann
CHEMICAL COMMUNICATIONS
(2007)