Article
Chemistry, Organic
Ya-Ping Wang, Xing-Ping Zhang, Ming-Sheng Xie, Hai-Ming Guo
Summary: In this study, highly enantioselective propargyl Claisen rearrangement of O-propargyl beta-ketoesters was achieved using a chiral cobalt complex as the catalyst under mild reaction conditions. A diverse range of chiral allenyl-substituted all-carbon quaternary beta-ketoesters were obtained in good yields and high enantioselectivities.
Review
Chemistry, Multidisciplinary
Andres Felipe Leon Rojas, Sara Helen Kyne, Philip Wai Hong Chan
Summary: Late-transition-metal-based complexes are essential catalysts in chemical synthesis, as they can rapidly and efficiently increase molecular complexity from readily accessible substrates. The control over product selectivities achieved by these catalysts, in terms of chemoselectivity, diastereoselectivity, enantioselectivity, and site-selectivity, is remarkable and has enabled a wide range of functional group transformations.
ACCOUNTS OF CHEMICAL RESEARCH
(2023)
Article
Chemistry, Physical
Ren-Xiao Liang, Chao Zhong, Zhi-Hong Liu, Miao Yang, Heng-Wei Tang, Jian-Fei Chen, Yun-Fang Yang, Yi-Xia Jia
Summary: Palladium-catalyzed intramolecular enantioselective beta-arylation of tetrasubstituted endocyclic and exocyclic enamines can lead to a range of optically active products with high enantiomeric ratios. Different bases and chiral ligands can be used to achieve different levels of enantioselectivity.
Article
Chemistry, Organic
Dharmendra Kumar, Dhananjay Chaudhary, Km Ishu, Suman Yadav, Naveen Kumar Maurya, Ruchir Kant, Malleswara Rao Kuram
Summary: A domino reaction sequence has been developed for the synthesis of pyrroloindolines, in which tryptamine derivatives and donor-acceptor diazo compounds are used as substrates. This reaction simultaneously forms three consecutive stereogenic centers, providing a convenient and efficient strategy for the construction of complex molecules. Copper catalysis enables the reaction to proceed smoothly at room temperature, and a wide range of substrates can be employed.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Yujie Dong, Jun Liu, Xing Gao, Ting Pan, Biming Mao, Songcheng Yu, Yongjun Wu, Cheng Zhang, Hongchao Guo
Summary: A palladium-catalyzed cascade cyclization was developed for the synthesis of biologically active tetracyclic dihydrocyclopentaindenofuranone derivatives. The reaction exhibited moderate to high yields and excellent diastereoselectivities, with the allene moiety fully fused into the cyclopentene ring.
CHINESE CHEMICAL LETTERS
(2023)
Article
Chemistry, Applied
Haixia Zhao, Yuchen Jiang, Tongqing Weng, Yongjia Shang, Jian Wang
Summary: A three component construction of conjugated 1,3-dienes bearing oxindoles or isoquinolinediones from alkenylated aryl iodides, allenes and diazo compounds via a palladium catalyzed sequential alkene/allene/carbenoid insertion reaction was developed. Three C-C bonds were formed in high order, offering access to multi-substituted dienes in high yields and up to > 20:1 E/Z selectivities. The reaction features excellent functional groups tolerance under mild conditions.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Siti Nur Fairuz Binte Sheikh Ismail, Binmiao Yang, Yu Zhao
Summary: In this study, a highly diastereo- and enantioselective Pd-catalyzed [4 + 2] cycloaddition of benzofuran-derived azadienes with vinyl benzoxazinanones was successfully achieved, leading to the construction of a novel spirocyclic tetrahydroquinoline scaffold with high stereoselectivity.
Article
Chemistry, Organic
Zhongliang Cai, Junyi Zhou, Miao Yu, Liqin Jiang
Summary: The divergent chemoselective synthesis of 2-methylene-2,3-dihydrothiazoles and 4-benzylidene pyrrolidine-2-thiones (most with E stereoselectivity) from N-propargyl thiocarbamoyl fluorides and malonate esters has been accomplished, with one pathway providing 4-benzylidene pyrrolidine-2-thiones and another leading to 2-methylene-2,3-dihydrothiazoles through isomerization of alpha,alpha-diester thioamide intermediates.
Review
Chemistry, Organic
Mohini Shrestha, Xianqing Wu, Wenyi Huang, Jingping Qu, Yifeng Chen
Summary: This review article summarizes the development of carbamoyl chlorides as synthons for various amide-containing molecules and heterocycles in transition metal-catalyzed reactions. It highlights the advancements and applications of carbamoyl chlorides in organic framework synthesis, as well as briefly discusses the chemical behavior of their structural analogs.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Review
Chemistry, Multidisciplinary
Subhabrata Dutta, Trisha Bhattacharya, Daniel B. Werz, Debabrata Maiti
Summary: Allylation reactions, pioneered by Tsuji and Trost, are essential C-C bond-forming transformations with broad applications in synthetic chemistry, bioactive compounds, and pharmaceutical industries. The development of synthetic strategies and the emergence of site-selective C-H activation have further expanded the scope of allylation reactions, eliminating the need for pre-functionalized substrates and activated allylating reagents.
Article
Chemistry, Organic
Jonathan P. Knowles, Hannah G. Steeds, Maria Schwarz, Francesca Latter, Kevin Booker-Milburn
Summary: This method transforms simple starting materials into complex tetracyclic products with potential medicinal chemistry applications through a sophisticated chemical catalysis process.
Article
Chemistry, Multidisciplinary
Xiai Luo, Wenguang Li, Haiyan Lu, Guobo Deng, Yuan Yang, Chunming Yang, Yun Liang
Summary: This study achieved simultaneous C2-H arylation and C8-H alkylation of the naphthalene ring, providing an efficient method for synthesizing aryl-substituted spirocyclic oxindoles. The protocol enables three C-C bonds formation via intramolecular Heck reaction.
CHINESE CHEMICAL LETTERS
(2021)
Article
Chemistry, Organic
Chao Pei, Zhen Yang, Rene M. Koenigs
Summary: The photochemistry of palladium catalysis is an efficient strategy for cross coupling and multifunctionalization reaction of olefins via alkyl radicals. In this study, it has been demonstrated that isonitriles can act as radical acceptors and participate in a further radical cascade cyclization to produce phenanthridine derivatives. Moreover, this photocatalytic process has also been extended to cascade methylation reaction in one-pot using TMSCH2I as the radical precursor. Experimental and computational studies suggest that an intramolecular single electron transfer process is involved in the generation of alkyl radicals in this transformation.
Article
Chemistry, Organic
Fan Xiao, Peiqin Liao, Xiaoguang Lu, Jin Wang, Xiu-Qin Dong, Chun-Jiang Wang
Summary: In this study, an Ir-catalyzed asymmetric cascade reaction was successfully developed for the synthesis of chiral oxazinoindolone compounds with high efficiency. The method can be applied to pyrroles and other nitrogen-containing aromatic heterocycles. The reaction pathway was proposed based on preliminary mechanistic investigation. Importantly, the key intermediate for marine alkaloid (+)-agelastatin A can be readily accessed using this methodology.
Article
Chemistry, Multidisciplinary
Jie Lin, Minqiang Jia, Shengming Ma
Summary: The paper presents the successful development of the palladium-catalyzed exclusive 2,3-allenylation reaction of oxindoles with 2,3-allenylic carbonates, along with a proposed rationale for the selectivity of this reaction over the expected 1,3-alkadienylation.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Organic
Gregory Beutner, Ronald Carrasquillo, Peng Geng, Yi Hsiao, Eric C. Huang, Jacob Janey, Kishta Katipally, Sergei Kolotuchin, Thomas La Porte, Andrew Lee, Paul Lobben, Federico Lora-Gonzalez, Brendan Mack, Boguslaw Mudryk, Yuping Qiu, Xinhua Qian, Antonio Ramirez, Thomas M. Razler, Thorsten Rosner, Zhongping Shi, Eric Simmons, Jason Stevens, Jianji Wang, Carolyn Wei, Steven R. Wisniewski, Ye Zhu
Article
Multidisciplinary Sciences
Kyle W. Knouse, Justine N. deGruyter, Michael A. Schmidt, Bin Zheng, Julien C. Vantourout, Cian Kingston, Stephen E. Mercer, Ivar M. Mcdonald, Richard E. Olson, Ye Zhu, Chao Hang, Jason Zhu, Changxia Yuan, Qinggang Wang, Peter Park, Martin D. Eastgate, Phil S. Baran
Article
Chemistry, Organic
Bin Zheng, Chao Hang, Jason Zhu, Geoffrey E. Purdum, Melda Sezen-Edmonds, Daniel S. Treitler, Miao Yu, Changxia Yuan, Ye Zhu, Adam Freitag, Siwei Guo, Guanghui Zhu, Ben Hritzko, James Paulson, Jonathan G. Shackman, Brian L. He, Weiqing Fu, Hua Chia Tai, Sloan Ayers, Hyunsoo Park, Martin D. Eastgate, Ben Cohen, Amanda Rogers, Qinggang Wang, Michael A. Schmidt
Summary: A highly stereoselective synthesis of a cyclic dinucleotide STING agonist with two chiral thiophosphoramidate linkages is reported. This method efficiently and selectively introduces the rare and key functional groups using a specially designed P(V) reagent. Compared to the previous P(III) approach, this strategy provides a significantly higher yield of the CDN with reduced use of hazardous reagents and chromatographic purifications.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Martin J. Neal, Sarah L. Hejnosz, Jeffrey J. Rohde, Jeffrey D. Evanseck, Thomas D. Montgomery
Summary: This study reveals an alternative mechanistic pathway to explain experimental results and guide the development of new reagents, providing a more direct route for improving the use of N-oxides in generating azomethine ylide-dilithium oxide complexes.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yazhou Lou, Junqiang Wei, Mingfeng Li, Ye Zhu
Summary: This study reports an asymmetric reaction that establishes chirality at a remote position by using electrostatic steering to exert stereocontrol on the substrate. It demonstrates the achievement of precise long-range stereocontrol through ionic substrate-ligand interactions.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Samuel R. Zarcone, Hana J. Yarbrough, Martin J. Neal, Jordan C. Kelly, Katie L. Kaczynski, Aaron J. Bloomfield, Geoffrey M. Bowers, Thomas D. Montgomery, Daniel T. Chase
Summary: Nitration of the 2- and 6-positions in aza-BODIPYs can significantly impact their absorption and emission profiles, resulting in exceptional photophysical tunability and near-IR emission.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Thomas D. Montgomery, Joanne Rae Buchbinder, Ellen S. Gawalt, Robbie J. Iuliucci, Andrew S. Koch, Evangelia Kotsikorou, Patrick E. Lackey, Min Soo Lim, Jeffrey Joseph Rohde, Alexander J. Rupprecht, Matthew N. Srnec, Brandon Vernier, Jeffrey D. Evanseck
Summary: Scientific success in chemistry relies on the mastery of soft skills such as scientific writing and speaking. However, undergraduate students often lack training in scientific communication, leading to difficulties in expressing themselves clearly and logically. This article introduces a methodology that combines undergraduate research with the scientific method to provide students with a framework for effective communication. By challenging students to think deeply and focus on the essential components of the scientific method through written and oral assignments, they are able to improve their writing and speaking skills. Over the past decade, this approach has resulted in qualitative and quantitative gains in students' confidence and abilities, preparing them for future careers as scientists.
JOURNAL OF CHEMICAL EDUCATION
(2022)
Article
Chemistry, Multidisciplinary
Mingfeng Li, Xiu Li Chia, Chong Tian, Ye Zhu
Summary: This study presents a catalyst-controlled strategy that decouples the creation of mechanical chirality and the assembly of interlocked bonds. By using a novel class of anionic chiral phosphine ligands, enantioselective access to various mechanically planar chiral rotaxanes is achieved in Pd-catalyzed Suzuki-Miyaura reactions. The results demonstrate that precise catalytic stereocontrol over mechanical chirality can be achieved through distal ionic substrate-catalyst interactions, despite the noncovalent nature of the interlocking stereogenic elements.
Article
Biochemistry & Molecular Biology
Aiden M. Lane, Ny T. C. Luong, Jordan C. Kelly, Martin J. Neal, Jeremiah Jamrom, Aaron J. Bloomfield, Paul A. Lummis, Thomas D. Montgomery, Daniel T. Chase
Summary: A series of metal chelates containing the underexplored bis(phenolate) aza-dipyrromethene core were synthesized. These compounds showed high quantum yield for absorption and emission in near-infrared range. X-ray diffraction analysis revealed octahedral geometry for heavier group 13 metal chelates and tetrahedral geometry for boron chelates.
Article
Chemistry, Organic
Sarah L. Hejnosz, Danielle R. Beres, Alexander H. Cocolas, Martin J. Neal, Benjamin S. Musiak, Marianne M. B. Hanna, Aaron J. Bloomfield, Thomas D. Montgomery
Summary: We have developed a one-pot synthetic method for producing 1,2-diamines from easily prepared and commercially available precursors through a formal umpolung process. Our method utilizes an efficient [3 + 2] cycloaddition as the key step in forming substituted 1,2-diamines in moderate to high yields. These resulting compounds can undergo subsequent transformations, demonstrating their utility as synthetic building blocks for more complex scaffolds. Finally, we propose a reasonable mechanism for this transformation using density functional theory modeling, justifying the experimental observations.
Article
Chemistry, Organic
Ivan K. W. On, Ye Zhu
Summary: Enzymes and chemists both use noncovalent interactions to achieve stereoselective transformations. Chemists have developed chiral catalysts with ionic groups to facilitate electrostatic interactions for enantioselective reactions. This article summarizes recent efforts to develop phosphine ligands with noncoordinating ionic groups for long-range stereocontrol in Suzuki-Miyaura reactions.
Article
Chemistry, Organic
Ivan Keng Wee On, Wenyang Hong, Ye Zhu
Summary: Enzymes utilize non-covalent interactions to achieve precise site-selectivity and stereoselectivity in transformations. This study demonstrates the use of a chiral ionic ligand to facilitate remote selectivity and enantioselectivity through electrostatic steering, enabling an ionic-directed remote meta-selective atroposelective Suzuki-Miyaura coupling.
TETRAHEDRON LETTERS
(2023)
Article
Chemistry, Multidisciplinary
Junqiang Wei, Vincent Gandon, Ye Zhu
Summary: Synthetic application of asymmetric catalysis requires strategic alignment of bond construction and chiral target molecule creation. Remote desymmetrization offers advantages in spatial decoupling of catalytic transformation and generation of stereogenic element. However, this spatial separation presents challenges for chiral catalysts to discriminate distant enantiotopic sites several bonds away from a prochirality center.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Physical
Ivan Keng Wee On, Wenyang Hong, Ye Zhu
Summary: Atropisomerism, arising from a rotationally restricted bond, is common in natural products, functional materials, and pharmaceuticals. The development of an ionic interaction-directed atroposelective Suzuki-Miyaura coupling achieves unprecedented stereocontrol through catalyst-substrate interactions. The study demonstrates that high atroposelectivity can be achieved by engaging distal meta-substituents as the dominant stereocontrol elements, surmounting the influence of proximal ortho-groups.
Article
Chemistry, Multidisciplinary
Mingfeng Li, Xiu Li Chia, Ye Zhu
Summary: This study successfully achieved the overriding of innate regioselectivity in Pd-catalyzed reactions by using engineered covalently tethered transition metal-photocatalysts.
CHEMICAL COMMUNICATIONS
(2022)
