Article
Chemistry, Multidisciplinary
Kan-Lei Ji, Shu-Fan He, Dong-Dong Xu, Wen-Xin He, Jian-Feng Zheng, Pei-Qiang Huang
Summary: A concise asymmetric total synthesis of (-)-quinocarcin has been achieved through high step economy using commercially available starting materials. The key chiral pyrrolidine intermediate with three stereocenters was prepared via a catalytic enantioselective reductive 1,3-dipolar cycloaddition reaction. This synthesis also involved a Rh-III-catalyzed C-H activation/cyclization and a tandem diastereoselective hydrogenation/cyclization to construct the tetrahydroisoquinoline-pyrrolidine tetracyclic core unit of quinocarcin.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Cheng Wang, Yukun Guan
Summary: A concise total synthesis of (+)-aphanorphine was achieved in six steps, utilizing key features such as Pd-catalyzed intermolecular trimethylenemethane [3+2]-cycloaddition for forming ring C and Co-catalyzed radical cyclization through hydrogen-atom transfer to close ring B.
Article
Chemistry, Multidisciplinary
Morgane de Robichon, Thilo Kratz, Frederike Beyer, Julian Zuber, Christian Merten, Thorsten Bach
Summary: Substituted bicyclo[1.1.0]butanes add enantioselectively to 2(1H)-quinolones upon irradiation, leading to the formation of products with a chiral bicyclo[2.1.1]hexane skeleton. A two-point hydrogen bond between the quinolone and the template is responsible for stereocontrol in the photocycloaddition reaction. The chiral template can be recovered and reused, and sensitization is a suitable tool for performing the reaction with visible light.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Chu-Hong Ou, Ying-Ming Pan, Hai-Tao Tang
Summary: In this study, we designed and synthesized a porous organic polymer with NHC as the core structure, which exhibited higher catalytic activity and recyclability compared to homogeneous NHC. The polymer successfully catalyzed the cycloaddition reaction of aldehyde and ethyl isocyanoacetate under electro-oxidation conditions. This study provides a reference for the development of new green catalytic systems.
SCIENCE CHINA-CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Tingting Li, Zhichao Jin, Yonggui Robin Chi
Summary: This review discusses N-heterocyclic carbene-catalyzed reactions for the formation of aromatic compounds, categorizing them into 4 types based on activation modes. The achievements, challenges, and future research directions in NHC-catalyzed arene construction processes are summarized. The outlook is based on the authors' opinions and knowledge on the trends of NHC organocatalysis development.
SCIENCE CHINA-CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Niklas Rauscher, Line Noesborg, Christian Jandl, Thorsten Bach
Summary: In this study, the prezizane-type sesquiterpene agarozizanol B was synthesized through a photochemical cascade reaction, successfully achieving the key step of the synthesis with a specific strategy and obtaining the (+)-enantiomer that is identical to the natural product.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Tuong Anh To, Chao Pei, Rene M. Koenigs, Thanh Vinh Nguyen
Summary: In this study, the promotion of carbonyl-olefin metathesis reactions by hydrogen-bonding-assisted Bronsted acid catalysis was investigated. The role of hexafluoroisopropanol (HFIP) solvent in assisting the pTSA Bronsted acid catalyst and the current limitations of the carbonyl-olefin metathesis reaction were revealed through experimental and computational mechanistic studies.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Mingkai Zhang, Peilin Xu, Alex J. Vendola, Christophe Allais, Anne-Marie Dechert Schmitt, Robert A. Singer, James P. Morken
Summary: This paper describes an easily synthesized chiral diazaborolidine that is inexpensive, stable, and exhibits excellent stereoselection across multiple reaction classes. These versatile compounds have utility in four different classes of cycloaddition reactions, offering good yield and stereoselectivity. X-ray structure analysis provides insight into the origin of stereocontrol.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Physical
Robert Francke, R. Daniel Little
Summary: Electrochemical catalysis is a valuable method for conducting redox-neutral reactions at mild conditions. It involves injecting electrons or holes into the reactant to induce chemical transformations. Recent advances have been made in understanding the mechanisms and developing new applications in this field. This contribution summarizes the recent progress in electrochemical catalysis.
CURRENT OPINION IN ELECTROCHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Chaohuang Chen, Constantin G. Daniliuc, Gerald Kehr, Gerhard Erker
Summary: The synthesis of element-carbon double bonds is described in this passage, focusing on the reactions with various molecules to form annulated heterocycles.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Xinyao Li, Johannes Grosskopf, Christian Jandl, Thorsten Bach
Summary: 3-Substituted quinoxalin-2(1H)-ones and various aryl-substituted or tethered olefins can undergo an enantioselective aza Paterno-Buchi reaction upon irradiation with a chiral sensitizer at lambda=420 nm. The absolute and relative configuration of the products were elucidated by X-ray crystallography, suggesting triplet energy transfer in a hydrogen-bonded complex between the imine substrate and the catalyst. Preliminary experiments also explored intramolecular cycloaddition and alternative reaction modes of quinoxalinones.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Organic
Yi-Ren Zhu, Jie Xu, Hui-Fang Jiang, Rui-Jing Fang, Yan-Jun Zhang, Lu Chen, Chen Sun, Fei Xiong
Summary: This article reviews the application of bifunctional sulfonamide as a hydrogen-bonding catalyst in asymmetric organocatalysis after 2011, highlighting asymmetric processes such as aldol reaction, Michael addition, Mannich reaction, desymmetrization, and cyclization.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Fangfang Guo, Jiean Chen, Yong Huang
Summary: Recently, chiral N-heterocyclic carbenes (NHCs) have been established as powerful catalysts for enantioselective bond-forming processes via noncovalent interactions. A bifunctional NHC with an embedded hydrogen-bonding motif has been reported in this study, showing remarkable tolerance of various Michael acceptors in an asymmetric aza-conjugate addition reaction, with catalytic efficiency far exceeding that of the benchmark tertiary amine-thiourea scaffold.
Article
Chemistry, Multidisciplinary
Xiangjin Kong, Pan-Pan Zhou, Yao Wang
Summary: This study introduces the concept of chalcogen...pi bonding catalysis, which activates molecules of pi systems through interaction between chalcogen and pi-electron cloud. The experimental results demonstrate that S...pi and Se...pi bonding interaction can efficiently drive the cycloaddition reaction, with double Se...pi bonding interaction influencing the stereoselectivity of the process.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Hunter S. Sims, Pedro Andrade Horn, Ryota Isshiki, Melissa Lim, Yan Xu, Robert H. Grubbs, Mingji Dai
Summary: The concise and stereoselective total synthesis of the clinically relevant tricyclic prostaglandin D-2 metabolite methyl ester was achieved in eight steps using a variety of organic reactions. The synthesis also accumulated a significant amount of valuable material for clinical research purposes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Ken S. Feldman, Inanllely Y. Gonzalez, Christopher M. Glinkerman
JOURNAL OF ORGANIC CHEMISTRY
(2015)
Article
Chemistry, Organic
Christopher M. Glinkerman, Dale L. Boger
Article
Chemistry, Organic
Kiyoun Lee, Yam B. Poudel, Christopher M. Glinkerman, Dale L. Boger
Article
Chemistry, Organic
Ryan E. Quinones, Christopher M. Glinkerman, Kaicheng Zhu, Dale L. Boger
Article
Chemistry, Organic
Christopher M. Glinkerman, Dale L. Boger
Article
Chemistry, Multidisciplinary
Ken S. Feldman, Inanllely Y. Gonzalez, Christopher M. Glinkerman
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2014)
Article
Chemistry, Organic
Erin D. Anderson, Adam S. Duerfeldt, Kaicheng Zhu, Christopher M. Glinkerman, Dale L. Boger
Article
Hematology
Stosh Ozog, Nina D. Timberlake, Kip Hermann, Olivia Garijo, Kevin G. Haworth, Guoli Shi, Christopher M. Glinkerman, Lauren E. Schefter, Saritha D'Souza, Elizabeth Simpson, Gabriella Sghia-Hughes, Raymond R. Carillo, Dale L. Boger, Hans-Peter Kiem, Igor Slukvin, Byoung Y. Ryu, Brian P. Sorrentino, Jennifer E. Adair, Scott A. Snyder, Alex A. Compton, Bruce E. Torbett
Article
Biochemistry & Molecular Biology
Michael P. Torrens-Spence, Anastassia Bobokalonova, Valentina Carballo, Christopher M. Glinkerman, Tomas Pluskal, Amber Shen, Jing-Ke Weng
Article
Biochemistry & Molecular Biology
Alicia J. Angelbello, Mary E. Defeo, Christopher M. Glinkerman, Dale L. Boger, Matthew D. Disney
ACS CHEMICAL BIOLOGY
(2020)
Article
Multidisciplinary Sciences
Colin Y. Kim, Andrew J. Mitchell, Christopher M. Glinkerman, Fu-Shuang Li, Tomas Pluskal, Jing-Ke Weng
NATURE COMMUNICATIONS
(2020)
Article
Chemistry, Multidisciplinary
Zixi Zhu, Christopher M. Glinkerman, Dale L. Boger
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Review
Plant Sciences
Michael P. Torrens-Spence, Christopher M. Glinkerman, Jan Gunther, Jing-Ke Weng
Summary: Imine chemistry plays a crucial role in plant metabolism, involving the biosynthesis of plant natural products and evolution of plant metabolic enzymes. A better understanding of plant imine chemistry will help expand the scope of imine natural product biosynthesis for diverse biotechnological applications.
CURRENT OPINION IN PLANT BIOLOGY
(2021)
Article
Chemistry, Multidisciplinary
Christopher M. Glinkerman, Shaoting Lin, Jiahua Ni, Fu-Shuang Li, Xuanhe Zhao, Jing-Ke Weng
Summary: In this study, several sporopollenin analogues were synthesized and characterized, confirming the proposed structural model and demonstrating favorable chemical, thermal, and mechanical properties. This research explores a new design framework for robust materials inspired by natural sporopollenins, and provides insights and reagents for future elucidation and engineering of sporopollenin biosynthesis in plants.
COMMUNICATIONS CHEMISTRY
(2022)