Article
Chemistry, Organic
Daiki Ishii, Shin-ichi Hirashima, Kosuke Nakashima, Hiroshi Akutsu, Takaaki Sakai, Yasuyuki Matsushima, Masahiro Kawada, Tsuyoshi Miura
Summary: A new organocatalyst efficiently promotes the asymmetric direct vinylogous conjugate additions of alpha-angelica lactones to benzoyl acrylonitrile derivatives, resulting in products with excellent enantioselectivities. The chiral gamma,gamma-disubstituted gamma-butenolides obtained can be readily transformed to valuable synthetic intermediates.
Article
Chemistry, Organic
Laxman Devidas Khalse, Sachin S. Gorad, Prasanta Ghorai
Summary: In this study, a new Cu(II)-(S,S)-Pr-i-FOXAP catalyst was reported for the borylative Michael/Michael addition cascade cyclization of unsymmetrical dienone, leading to the synthesis of highly substituted and functionalized spiroindane boronates under mild conditions. A series of optically active spiroids bearing boronic ester were obtained with excellent yields and good to excellent enantioselectivities and diastereoselectivities.
Article
Chemistry, Organic
Daeil Bae, Jin Won Lee, Do Hyun Ryu
Summary: New bifunctional secondary amine organocatalysts derived from L-proline were synthesized and applied in enantioselective Michael reactions in water, yielding high product yields and stereoselectivity. Investigations on the effect of phenyl group at (R)-C6 in the catalyst were conducted, and the successful formal synthesis of a novel histamine H3 receptor agonist, Sch 50971, demonstrated the synthetic utility of this reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Yu-Hang Miao, Yuan-Zhao Hua, Shi-Kun Jia, Xiao Xiao, Min-Can Wang, Guang-Jian Mei
Summary: The first Zn-ProPhenol catalyzed asymmetric inverse-electron-demand Diels-Alder reaction has been successfully achieved. This method employs a dual-activation mode under mild conditions, enabling the synthesis of diverse biologically important dihydropyrans in high yields and excellent stereoselectivities.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Andrea Chaves-Pouso, Andres M. Alvarez-Constantino, Martin Fananas-Mastral
Summary: Allylic gem-dichlorides can be efficient substrates for catalytic asymmetric allylboration of alkynes. The method generates chiral skipped dienes with excellent levels of chemo-, regio- enantio- and diastereoselectivity, making them versatile building blocks for the synthesis of optically active compounds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Sadhanendu Samanta, Jin Cui, Hidetoshi Noda, Takumi Watanabe, Masakatsu Shibasaki
Summary: In this study, a gram-scale syn-selective asymmetric vinylogous addition of butenolides to chromones was developed using an Al-Li-BINOL (ALB) complex catalyst. The reaction showed high diastereoselectivity with ratios up to 20:1 and enantioselectivity of 84-98% for various substrate combinations. This method is complementary to previous reports and improves selectivity for several chromones. Computational studies support the role of ALB as a bifunctional catalyst in this reaction and provide insights into the origin of the observed stereoselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Yi Li, Shuang Xin, Rui Weng, Xiaohua Liu, Xiaoming Feng
Summary: Chiral chromanone lactones are important natural products with significant biological activity. In this study, we developed a direct diastereo- and enantioselective vinylogous conjugate addition of butenolide to 2-ester substituted chromones. The reaction demonstrated good efficiency and selectivity, providing the desired products in high yield and excellent enantioselectivity.
Article
Chemistry, Multidisciplinary
Andrea Chaves-Pouso, Andres M. Alvarez-Constantino, Martin Fananas-Mastral
Summary: In this Communication, Martin Fananas-Mastral et al. report an enantio- and diastereoselective copper-catalyzed allylboration of alkynes with allylic gem-dichlorides.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Fang Xie, Jie Zhao, Deyue Ren, Jianming Xue, Jingyi Wang, Qin Zhao, Lu Liu, Xiaodan Liu
Summary: A Cu-catalyzed coupling reaction between cyclic imino esters and 2H-azirines has been developed, allowing for the synthesis of novel optically active aziridines in high yields and with excellent levels of diastereo- and enantioselectivities under mild conditions. This method features a broad substrate scope, good functional group compatibility, and enriches the existing reaction type for the rapid synthesis of optically active aziridines bearing vicinal tetrasubstituted stereogenic carbon centers.
Article
Chemistry, Multidisciplinary
Jian Chen, Lifu Wu, Yue Zhao, Shaolin Zhu
Summary: In this study, we report a catalytic reaction that can control two stereocenters simultaneously. By using a chiral catalyst, we achieved simultaneous control of the stereocenters in two substrates, resulting in the formation of high-value products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Lalitha Gummidi, Altaf Muddassar, Gangavaram V. M. Sharma, V Murugesh, Surisetti Suresh
Summary: A novel synthesis strategy was proposed for the formation of N-bridged pyridine fused quinolone derivatives via a tandem reaction, which not only constructs multiple bonds in a single operation but also proceeds under transition metal-free conditions, demonstrating broad substrate scope and gram scale synthesis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Esteban Matador, Javier Iglesias-Siguenza, David Monge, Pedro Merino, Rosario Fernandez, Jose M. Lassaletta
Summary: A highly enantio- and diastereoselective thiourea-catalyzed dearomatization of isoquinolines has been developed using N-tert-butylhydrazones as key neutral reagents, leading to the formation of appealing dihydroisoquinoline derivatives with excellent stereocontrol. Experimental and computational data support the generation of highly ordered complexes that play a crucial role in the selective and high-yielding transformations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Hyun Ji Jeon, Su Min Park, Yu Lim Lee, Sang-gi Lee
Summary: The palladium-catalyzed divergent asymmetric synthesis of chiral spiro-furanindoline derivatives is described. The zwitterionic alkoxy pi-allyl Pd(II) intermediate, generated catalytically from vinyl ethylene carbonate (VEC), could undergo ligand-controlled enantio-and diastereoselective dipolar [3 + 2] spiroannulation with indole-based azadienes to afford the optically active spiro-furanindolines embedding an all-carbon quaternary stereocenter in high yields (up to 99%) with good to excellent stereoselectivities (up to 99% ee and up to >94:6 dr).
Article
Chemistry, Organic
Meng Li, Guang-Rui Peng, Xuan Yang, Zhen-Ning Ma, Jian-Bo Xie
Summary: We developed a copper-catalyzed enantio- and diastereoselective boron conjugate addition method for α-alkyl α,beta-unsaturated esters under base-free conditions. The approach exhibited excellent enantioselectivities and moderate to good conversions, although with moderate diastereoselectivities. The synthetic utility of this protocol was demonstrated.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Zhenli Luo, Zhewei Li, Haoqiang Zhao, Ji Yang, Lijin Xu, Ming Lei, Qinghua Fan, Patrick J. Walsh
Summary: Significant progress has been made in the efficient synthesis of enantioenriched 1,2,3,4-tetrahydroquinoxalines in recent years. However, the access to trans-2,3-disubstituted 1,2,3,4-tetrahydroquinoxalines with enantio- and diastereoselectivity remains largely unexplored. In this study, a frustrated Lewis pair-based catalyst was used to achieve the one-pot tandem cyclization/hydrosilylation of 1,2-diaminobenzenes and 1,2-diketones, resulting in high yields of trans-2,3-disubstituted 1,2,3,4-tetrahydroquinoxalines with excellent diastereoselectivities. The reaction can be rendered asymmetric by using an enantioenriched borane-based catalyst, leading to enantioenriched products with high yields and complete diastereo- and enantiocontrol. The mechanistic pathway and the origin of the excellent stereoselectivity were elucidated through experiments and calculations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Multidisciplinary
Barry M. Trost, Chao-I (Joey) Hung, Guillaume Mata
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Multidisciplinary
Barry M. Trost, Jacob S. Tracy, Tas Yusoontorn, Chao-I Joey Hung
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Review
Chemistry, Multidisciplinary
Barry M. Trost, Christopher A. Kalnmals
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Article
Chemistry, Organic
Barry M. Trost, Chao-I Joey Hung, Guillaume Mata, Ying Liu, Yiye Lu, Elumalai Gnanamani
Article
Chemistry, Multidisciplinary
Barry M. Trost, James J. Cregg, Christoph Hohn, Wen-Ju Bai, Guoting Zhang, Jacob S. Tracy
Article
Chemistry, Organic
Barry M. Trost, Christopher A. Kalnmals, Divya Ramakrishnan, Michael C. Ryan, Rebecca W. Smaha, Sean Parkin
Review
Chemistry, Multidisciplinary
Barry M. Trost, Jacob S. Tracy
ACCOUNTS OF CHEMICAL RESEARCH
(2020)
Review
Chemistry, Multidisciplinary
Jacob S. Tracy, Christopher A. Kalnmals, F. Dean Toste
Summary: Professor Barry M. Trost has made significant contributions in the fields of synthetic method development and complex molecule total synthesis during his fifty-five year tenure. While some of his lesser-known reactions may not be as prominent as others, they are no less important and have been widely adopted by the synthetic community.
ISRAEL JOURNAL OF CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Guillaume Mata, Christopher A. Kalnmals
Summary: Prof. Barry M. Trost has shown an exceptional interest in complex molecule synthesis throughout his independent career, leading to the synthesis of over 260 natural products, pharmaceuticals, and complex biomolecules over the past 55 years. Remarkably, more than half of this output was achieved in the last twenty years, showcasing Trost's inventiveness and ingenuity. This review provides a brief summary of all total syntheses from the Trost laboratories since 2000, highlighting sixteen particularly notable campaigns in the field.
ISRAEL JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Organic
Barry M. Trost, Benjamin R. Taft, Jacob S. Tracy, Craig E. Stivala
Summary: The synthesis of the pentacylic core of (+)-cit-rinadin A was described using palladium-catalyzed trimethylenemethane chemistry. The key spirooxindole motif was formed in a catalytic, asymmetric fashion, with subsequent addition of the piperidine ring and final ring formation through an intramolecular displacement reaction.
Article
Agriculture, Multidisciplinary
Christopher A. Kalnmals, Zoltan L. Benko, Adel Hamza, Karla Bravo-Altamirano, Thomas L. Siddall, Moriah Zielinski, Hudson K. Takano, Dilpreet S. Riar, Norbert M. Satchivi, Joshua J. Roth, Jeffrey B. Church
Summary: In this study, we developed a novel class of diaryl ether herbicides. After optimization, several molecules with improved control over broadleaf and grass weeds were discovered. A three-step combinatorial approach was initially employed, followed by a one-step Ullmann-type coupling for faster access to new analogs. The primary target of these diaryl ethers was found to be acetolactate synthase (ALS), and a scaffold hopping campaign using a copper-catalyzed methodology was conducted to explore alternative modes of action with reduced resistance cases. Our investigation revealed that while ALS inhibition is the exclusive mechanism of herbicidal activity in this class, our molecules represent a structurally distinct Group 2 herbicides. The structure-activity relationships leading to this conclusion are described herein.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2023)
Article
Agriculture, Multidisciplinary
Hudson K. Takano, Zoltan L. Benko, Moriah M. Zielinski, Adel Hamza, Christopher A. Kalnmals, Joshua J. Roth, Karla Bravo-Altamirano, Thomas Siddall, Norbert Satchivi, Jeffrey B. Church, Dilpreet S. Riar
Summary: Herbicides are effective tools for managing weeds and ensuring food production. Corteva Agriscience R&D has discovered new diphenyl-ether compounds with excellent postemergent efficacy on important weed species and corn safety. Through research in chemistry, biology, biochemistry, and computational modeling, the primary mode of action for these compounds was elucidated as targeting the acetolactate synthase (ALS) enzyme. These compounds have a unique biochemical profile and show excellent herbicidal activity and corn selectivity, making them a significant development in the search for novel, safe, and sustainable weed control solutions.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Wenhao Zhang, Ryan Walser-Kuntz, Jacob S. Tracy, Tim K. Schramm, James Shee, Martin Head-Gordon, Gan Chen, Brett A. Helms, Melanie S. Sanford, F. Dean Toste
Summary: Redox flow batteries (RFBs) are a promising technology for energy storage. This study introduces a new organic scaffold, indolo[2,3-b]quinoxaline, as a stable and high-performance anolyte for nonaqueous RFBs. When paired with MEEPT, it achieves a 2.3 V all-organic RFB.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Jacob S. Tracy, Elena S. Horst, Vladislav A. Roytman, F. Dean Toste
Summary: All-organic non-aqueous redox flow batteries (O-NRFBs) are a promising technology for grid-scale energy storage. However, most high-voltage O-NRFBs suffer from crossover of redox active material, resulting in reduced energy density and capacity. This study presents the development of a new class of bipolar redox active materials for symmetric flow batteries, which shows higher cell voltages than non-coupled building blocks. The superior performance of symmetric O-NRFBs is confirmed by comparing it with an asymmetric flow battery.
