Article
Chemistry, Applied
Liang Xu, Jia Cui, Shan Gao, Jianjun Wang, Jiao Liu, Hongge Jia, Zhuanfang Zhang, Fengjuan Miao, Yu Zang
Summary: Chiral conjugated microporous polymers (CCMPs) containing amide groups were designed and synthesized for the first time as heterogeneous asymmetric catalyst platforms for the stabilization of Pd in asymmetric catalytic synthesis. Four Pd/CCMPs heterogeneous catalysts exhibited efficient catalytic activity and excellent enantioselectivity in the asymmetric Henry reaction, with a wide range of substrates and easy recovery. The Pd/CCMPs composites could be easily recycled and maintained catalytic activity after 3 cycles of reactions.
MICROPOROUS AND MESOPOROUS MATERIALS
(2022)
Article
Chemistry, Multidisciplinary
Muhammad Sohail, Fujie Tanaka
Summary: The DYKAT reactions can transform dihydrobenzofuranone derivatives into spirooxindole derivatives with high enantioselectivities and yields, regardless of the stereochemistry of the starting materials.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Yingqi Xia, Yingtang Ning, Minjie Liu, Fen -Er Chen
Summary: A poly(ethylene glycol) supported amino alcohol has been developed as a chiral ligand for the copper-catalyzed asymmetric nitrolaldol reaction. The catalyst enables the synthesis of syn-2-nitro-1,3-diols with high yields and stereoselectivities. The PEG moiety allows for easy purification and recycling of the catalyst.
JOURNAL OF CATALYSIS
(2023)
Article
Chemistry, Applied
Marcia R. R. Renio, Francisco J. P. M. Sousa, Nelia C. T. Tavares, Artur J. M. Valente, M. Elisa da Silva Serra, Dina Murtinho
Summary: The enantioselective Henry reaction is an important carbon-carbon bond forming reaction that requires the use of efficient chiral catalysts. In this study, in situ formed complexes of N-substituted dihydroxypyrrolidines were evaluated as catalysts, showing that the nature of the N-substituent significantly influences the outcome of the reaction. Best results were obtained using a Cu (II) complex of (3S,4S)-N-benzyl-3,4-dihydroxypyrrolidine, with products having er up to 92:8 (R:S).
APPLIED ORGANOMETALLIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Teng Yuan, Kelton Radefeld, Chuan Shan, Carter Wegner, Erin Nichols, Xiaohan Ye, Qi Tang, Lukasz Wojtas, Xiaodong Shi
Summary: Here, we have reported an intermolecular asymmetric hydrative aldol reaction by using a vinyl-gold intermediate under ambient conditions. This reaction provides a base-free approach to β-hydroxy amides with high efficiency, yielding up to 95% and with over 50 examples. The use of vinyl gold intermediate as a reactive nucleophile and Fe(acac)(3) as a critical co-catalyst prevents undesired protodeauration, allowing the transformation to proceed under mild conditions with excellent functional group tolerance and stereoselectivity (>20:1 d.r. and up to 99% ee).
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Ken-Loon Choo, Bijan Mirabi, Karl Z. Demmans, Mark Lautens
Summary: Enantioenriched spiro-oxiranes with three contiguous stereocenters were synthesized using a rhodium-catalyzed cascade reaction, enabling the formation of a spirocyclic framework in a single step. Both sp(2)- and sp-hybridized carbon nucleophiles were found to be efficient initiators, yielding products with different functional groups. Derivatization studies demonstrated the synthetic versatility of the products' epoxide and alkyne moieties. DFT calculations were employed to explain spectroscopic discrepancies between solution- and solid-state structures of the products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Chao Yao, Yaoqi Chen, Chao Wang, Ruize Sun, Haotian Chang, Ruiheng Jiang, Lin Li, Xin Wang, Yue-Ming Li
Summary: Chiral O-N-N tridentate ligands designed from proline and BINOL were evaluated for their performance in a copper(II)-catalyzed asymmetric Henry reaction. The study found that the stereoselectivity of the reaction could be controlled by adjusting the structure and substituents of the ligand.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Alessandra Puglisi, Sergio Rossi, Fabian Herbrik, Fabrizio Medici, Maurizio Benaglia
Summary: This article presents the use of enabling technologies in the stereoselective synthesis of enantioenriched compounds, with a particular focus on the most significant contributions in this field in recent years.
GREEN PROCESSING AND SYNTHESIS
(2021)
Article
Chemistry, Multidisciplinary
Shu-Sen Li, Shuo Sun, Jianbo Wang
Summary: The catalytic asymmetric trifluoromethylation of cyclic ketones via a Sc-III/chiral bisoxazoline-catalyzed homologation reaction using 2,2,2-trifluorodiazoethane (CF3CHN2) as the CF3 source is an efficient method to generate chiral alpha-trifluoromethyl cyclic ketones with excellent diastereoselectivity and enantioselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Applied
Michael Franc, Ivana Cisarova, Jan Vesely
Summary: The present study investigates an enantioselective cyclization of enals with imidazolone derivatives catalyzed by a combination of achiral Pd(0) complex and chiral secondary amine. Corresponding spirocyclic imidazolones were produced in high yields with moderate diastereoselectivity and excellent enantioselectivity. The developed co-operative catalytic methodology provides a highly substituted spirocyclic scaffold with four stereogenic centers under mild conditions.
Article
Biochemistry & Molecular Biology
Evgeniy V. Suslov, Konstantin Y. Ponomarev, Oxana S. Patrusheva, Sergey O. Kuranov, Alina A. Okhina, Artem D. Rogachev, Aldar A. Munkuev, Roman V. Ottenbacher, Alexander I. Dalinger, Mikhail A. Kalinin, Sergey Z. Vatsadze, Konstantin P. Volcho, Nariman F. Salakhutdinov
Summary: A series of new chiral bispidines containing monoterpenoid fragments were synthesized and studied as ligands for Ni-catalyzed addition reactions. Conditions for chromatographic analysis were developed to separate the enantiomers of the synthesized chiral products. The bispidine-monoterpenoid conjugates were found to be effective ligands for reactions, but not chiral inducers, with the observation of significant formation of hydrogenation products in the presence of catalytic systems.
Article
Chemistry, Multidisciplinary
Chang-Sheng Wang, Qiao Sun, Felipe Garcia, Chen Wang, Naohiko Yoshikai
Summary: The study presents a simple and inexpensive catalytic system based on cobalt(II) iodide, 1,3-bis(diphenylphosphino)propane, and Zn for the [2+2+2] cycloaddition of various nitriles and diarylacetylenes to synthesize a broad range of polyarylated pyridines. DFT studies support a reaction pathway involving oxidative coupling of two alkynes, insertion of the nitrile into a cobaltacyclopentadiene, and C-N reductive elimination, leading to the synthesis of tetra- and pentaarylpyridines that can be used as precursors for nitrogen-containing polycyclic aromatic hydrocarbons.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Ling Zhao, Yicong Luo, Junzhe Xiao, Xiaohong Huo, Shengming Ma, Wanbin Zhang
Summary: The stereodivergent synthesis of allene compounds with adjacent chiralities has been achieved through Pd/Cu-catalyzed dynamic kinetic asymmetric alkylation. The matched reactivity of a bimetallic catalytic system allows for a smooth reaction of racemic aryl-substituted allenylic acetates with sterically crowded aldimine esters. Various chiral non-natural amino acids with a terminal allenyl group can be easily synthesized with high yields and excellent diastereo- and enantioselectivities.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
David Savary, Olivier Baudoin
Summary: C-H activation-based ring-forming methods are powerful for constructing complex molecular structures, especially useful for synthesizing chiral polycyclic aromatic hydrocarbons and other important organic electronic materials. A new enantioselective synthesis method using Pd-catalyzed C(sp(2))-H arylation protocol has been described, delivering diverse polycyclic compounds with high yield and good to excellent enantioselectivity, with investigation into their chiroptical properties.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Fei Tian, Wu-Lin Yang, Tao Ni, Jian Zhang, Wei-Ping Deng
Summary: The development of efficient methods for synthesizing chiral polycyclic indoles is crucial for their wide applications in medicines, pesticides, and other functional molecules. The study revealed novel indolyl substituted metal-allyl zwitterionic intermediates that could participate in asymmetric cycloaddition reactions with high selectivities, leading to the synthesis of diverse chiral polycyclic indoles.
SCIENCE CHINA-CHEMISTRY
(2021)
Article
Chemistry, Physical
Felix Prause, Benjamin Arensmeyer, Benjamin Froehlich, Matthias Breuning
CATALYSIS SCIENCE & TECHNOLOGY
(2015)
Article
Chemistry, Organic
Johannes Kaldun, Alexander Krimalowski, Matthias Breuning
TETRAHEDRON LETTERS
(2016)
Article
Chemistry, Multidisciplinary
Dagmar Scharnagel, Jessica Goller, Nicklas Deibl, Wolfgang Milius, Matthias Breuning
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2018)
Article
Chemistry, Multidisciplinary
Dagmar Scharnagel, Felix Prause, Johannes Kaldun, Robert G. Haase, Matthias Breuning
CHEMICAL COMMUNICATIONS
(2014)
Article
Chemistry, Organic
Matthias Breuning, David Hein
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2013)
Article
Chemistry, Organic
Felix Prause, Johannes Kaldun, Benjamin Arensmeyer, Benedikt Wennemann, Benjamin Froehlich, Dagmar Scharnagel, Matthias Breuning
SYNTHESIS-STUTTGART
(2015)
Article
Chemistry, Multidisciplinary
Giuseppe Zuccarello, Joan G. Mayans, Imma Escofet, Dagmar Scharnagel, Manila S. Kirillova, Alba H. Perez-Jimeno, Pilar Calleja, Jordan R. Boothe, Antonio M. Echavarren
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2019)
Article
Chemistry, Multidisciplinary
Dagmar Scharnagel, Imma Escofet, Helena Armengol-Relats, M. Elena de Orbe, J. Nepomuk Korber, Antonio M. Echavarren
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Physical
Johannes Kaldun, Felix Prause, Dagmar Scharnagel, Frederik Freitag, Matthias Breuning