Article
Chemistry, Multidisciplinary
Yinsong Zhao, Shaozhong Ge
Summary: A chromium-catalyzed reaction has been developed for the synthesis of boryl-functionalized skipped dienes. By utilizing a dimerization/hydroboration process, the target product can be obtained efficiently and with good selectivity. EPR spectroscopic studies suggest that the reaction proceeds through a chromium(I) hydride intermediate.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Sudheesh T. Sivanandan, Irishi N. N. Namboothiri
Summary: This study presents a facile, metal-free method for the synthesis of substituted alpha-carbolines from secondary Morita-Baylis-Hillman acetates of nitroalkenes. The regioselective cascade reaction of MBH acetates with tosyliminoindolines leads to the formation of various alpha-carbolines with a wide substrate scope. The reaction occurs under mild conditions and yields products in high amounts within a short reaction time, showing scalability and potential synthetic applications.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Caitilin McManus, Agamemnon E. Crumpton, Simon Aldridge
Summary: This study reports on the insertion of alkynes into heterometallic bonds, producing (aluminylalkenyl)copper compounds with differential reactivity at two derived M-C functions. Unique to this system is the control over isolable syn or anti dimetallated alkenes, achieved through either kinetic or thermodynamic control. Subsequent reaction with CO results in the formation of the first structurally characterized copper acyl compounds, aided by the cooperative reactivity of the proximal aluminium centre.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Xuan Huang, Huichao You, Fang Fang, Fan Wang, Zhong-Quan Liu
Summary: This study demonstrated an efficient and selective radical nitration of olefins with NaNO2, leading to the synthesis of various (E)-nitroolefins in high yields.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Xiangyu Tan, Qianqian Gu, Xingjiang Yang, Yingying Yang, Bingwei Hu, Shuai Mao, Jun Lin, Yi Jin
Summary: Here, a Pd-catalyzed reaction for the selective and diastereoselective synthesis of dendralenc-functionalized dihydrofurans using allenyl acetates is described. Mechanistic studies revealed the formation of an epoxide from a carbonyl bond through cycloaddition, which has practical and mechanistic significance for the construction of other bioactive heterocyclic epoxides. The research also highlights the utility and potential of allenic esters as C2 synthons and 1,2-biselectrophiles in cycloaddition reactions.
Article
Chemistry, Multidisciplinary
Andreea Zubas, Alina Ghinet, Sergiu Shova, Elena Bicu
Summary: This study demonstrates the effectiveness of 4-(trimethylsilyl)-3-butyn-2-one as a dipolarophile in the [3+2] cycloaddition reaction for obtaining non-silicon adducts, namely 1-acetylindolizines, from cycloimmonium salts. The study also found the presence of 1-acetyl-2-trimethylsilyl-indolizines and 1-trimethylsilyl-2-acetylindolizines as isomeric trimethylsilyl-containing adducts. A comparison was made between the performance of 4-(trimethylsilyl)-3-butyn-2-one and 3-butyn-2-one in the [3+2] cycloaddition reaction. The resulting 1-acetyl or 2-acetylindolizines were evaluated for their potential to inhibit NCI-60 cancer cell growth in vitro, comparing with previously described 3-acetyl or 1-carboxyethylindolizines.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Antonia Becker, Christian P. Grugel, Bernhard Breit
Summary: In this study, a new synthetic method is reported for the efficient preparation of biologically active compounds.
Article
Chemistry, Organic
Yun-Qian Zhang, You-Qin Jiang, Yong-Hao Wang, Cong Qi, Yong Ling, Yanan Zhang, Gong-Qing Liu
Summary: This study reports the three-component selenofunctionalization processes of olefins, diselenides, and sulfonamides using FP-OTf as a reaction promoter. Under optimal conditions, a wide range of vicinally functionalized selenide derivatives can be obtained with high yields and excellent functional group compatibilities. Mechanistic studies indicate that FP-OTf plays a key role in this selenofunctionalization process.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Analytical
Shengchen Lv, Donghui Liu, Xueke Liu, Zhiqiang Zhou, Peng Wang
Summary: Setting up effective analysis method is crucial for environmental monitoring. In this study, 4-aminophenol functionalized nitrogen and sulfur co-doped carbon quantum dots (AP-NSCDs) were synthesized and used as a fluorescent sensor for nitroalkene pesticide and medicine detection. The sensor exhibited high sensitivity, selectivity, and stability, with a wide linear range and low detection limit. It was successfully applied for detecting nitroalkene compounds in various samples. This method provides a rapid and sensitive approach for monitoring nitroalkene compounds in the environment and food.
MICROCHEMICAL JOURNAL
(2023)
Article
Chemistry, Organic
Shahnawaz Khan, Monish Arbaz Ansari, Maya Shankar Singh
Summary: This study presents a chemo- and regioselective cascade annulation between fi-ketothioamides and diazo-substituted hypervalent iodine reagents under transition-metal-free and base-free conditions at room temperature. A divergent construction of fused-heterocyclic scaffold thiazolothiadiazoles has been achieved with the advantages of operational simplicity, scalability, broad substrate compatibility, and mild reaction conditions. This one-pot strategy not only avoids potential toxicity but also broadens the arsenal of synthetic methods to obtain fused N,S-heterocyclic frameworks.
Article
Chemistry, Organic
Peter Langer
Summary: This article discusses the reactions and applications of the dianion of 1,1-diphenylacetone. A new allene synthesis was serendipitously discovered through the study of the regioselectivity of these reactions. Additionally, the reactions of allene dianions with various electrophiles have been investigated.
Article
Chemistry, Organic
Tsukasa Tawatari, Ritsuki Kato, Kiyosei Takasu, Hiroshi Takikawa
Summary: A variety of highly functionalized allenes and allenamides are prepared by intramolecular propargylic ene reactions of benzynes. Specific benzyne precursors are used as a platform to link with various propargyl alcohols via a Si-O bond, expanding the scope of this reaction. Additionally, a complete transmission of point to axial chirality is demonstrated, resulting in a chiral, nonracemic allenamide.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Organic
Toktam S. Shirazian, Hossein Zahedian Tejeneki, Ali Nikbakht, Frank Rominger, Saeed Balalaie
Summary: This study presents a novel method for synthesizing functionalized acridines using a base-promoted formal [4+2] cycloaddition reaction. The method exhibits high selectivity and efficiency, making it a valuable approach for the synthesis of acridine backbones.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Daniels Posevins, Aitor Bermejo-Lopez, Jan-E. Backvall
Summary: An iron-catalyzed cross-coupling reaction of propargyl ethers with Grignard reagents was disclosed, allowing for efficient chirality transfer and preparation of various fluoroalkyl allenes. Additionally, an iron-catalyzed cross-coupling of Grignard reagents with alpha-alkynyl oxetanes and tetrahydrofurans was demonstrated as a straightforward approach towards fully substituted beta- or gamma-allenols.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Emily R. Sherman, William R. Cassels, Jeffrey S. Johnson
Summary: Asymmetric Michael additions are powerful tools for synthesizing stereochemically complex products. In this Letter, crystalline ss-keto esters were used to achieve a two-phase, one-pot merger of an asymmetric Michael addition with a crystallization-induced diastereomer transformation.
Article
Chemistry, Multidisciplinary
Matthew J. O'Connor, Chunrui Sun, Xinyu Guan, Venkata R. Sabbasani, Daesung Lee
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2016)
Article
Chemistry, Multidisciplinary
Venkata R. Sabhasani, Hyunjin Lee, Yuanzhi Xia, Daesung Lee
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2016)
Article
Chemistry, Multidisciplinary
Venkata R. Sabbasani, Genping Huang, Yuanzhi Xia, Daesung Lee
CHEMISTRY-A EUROPEAN JOURNAL
(2015)
Article
Chemistry, Organic
Venkata R. Sabbasani, Daesung Lee
Article
Chemistry, Organic
Venkata R. Sabbasani, Sang Young Yun, Daesung Lee
ORGANIC CHEMISTRY FRONTIERS
(2016)
Article
Chemistry, Organic
Venkata R. Sabbasani, Saswata Gupta, Sang Young Yun, Daesung Lee
ORGANIC CHEMISTRY FRONTIERS
(2018)
Article
Chemistry, Organic
Yuanzhi Xia, Nam-Kyu Lee, Venkata R. Sabbasani, Saswata Gupta, Daesung Lee
ORGANIC CHEMISTRY FRONTIERS
(2018)
Article
Chemistry, Multidisciplinary
Venkata R. Sabbasani, Kung-Pern Wang, Matthew D. Streeter, David A. Spiegel
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
Article
Chemistry, Physical
Saswata Gupta, Venkata R. Sabbasani, Siyuan Su, Donald J. Wink, Daesung Lee
Summary: A variety of heteroatom-chelated ruthenium alkylidenes have been developed as metathesis-active catalysts, including structurally diverse alkene-chelated complexes. By tuning the stability and reactivity of these complexes based on common design principles, characteristic behaviors in different metathesis reactions can be demonstrated.
Article
Biochemistry & Molecular Biology
David F. Caianiello, Mengwen Zhang, Jason D. Ray, Rebecca A. Howell, Jake C. Swartzel, Emily M. J. Branham, Egor Chirkin, Venkata R. Sabbasani, Angela Z. Gong, David M. McDonald, Viswanathan Muthusamy, David A. Spiegel
Summary: Targeted protein degradation (TPD) is a promising therapeutic strategy, with MoDE-A technology enabling degradation of extracellular proteins. Experimental evidence shows the modularity of MoDE-A molecules in inducing specific protein depletion, opening up new possibilities for disease treatment.
NATURE CHEMICAL BIOLOGY
(2021)
Article
Multidisciplinary Sciences
Xiuxiu Lu, Venkata R. Sabbasani, Vasty Osei-Amponsa, Christine N. Evans, Julianna C. King, Sergey G. Tarasov, Marzena Dyba, Sudipto Das, King C. Chan, Charles D. Schwieters, Sulbha Choudhari, Caroline Fromont, Yongmei Zhao, Bao Tran, Xiang Chen, Hiroshi Matsuo, Thorkell Andresson, Raj Chari, Rolf E. Swenson, Nadya I. Tarasova, Kylie J. Walters
Summary: The authors have identified and characterized XL5, a lead compound that binds to the N-terminal Pru domain of human Rpn13 (hRpn13), solved the NMR structure of XL5-ligated hRpn13 Pru, and developed XL5-PROTACs that preferentially target an identified hRpn13 Pru fragment present in multiple myeloma cells.
NATURE COMMUNICATIONS
(2021)
Article
Chemistry, Analytical
Isaiah Adelabu, Jessica Ettedgui, Sameer M. Joshi, Shiraz Nantogma, Md Raduanul H. Chowdhury, Stephen McBride, Thomas Theis, Venkata R. Sabbasani, Mushti Chandrasekhar, Deepak Sail, Kazutoshi Yamamoto, Rolf E. Swenson, Murali C. Krishna, Boyd M. Goodson, Eduard Y. Chekmenev
Summary: Alpha-ketoglutarate is a vital biomolecule involved in various metabolic pathways, and abnormal metabolism of alpha-ketoglutarate is linked to cancer. This study successfully synthesized highly polarized alpha-ketoglutarate using isotopic labeling, which could potentially be used as a contrast agent for real-time metabolic imaging.
ANALYTICAL CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Edward A. deRamon, Venkata R. Sabbasani, Matthew D. Streeter, Yannan Liu, Timothy R. Newhouse, David M. McDonald, David A. Spiegel
Summary: Pentosinane, a complex nonenzymatic post-translational modification of proteins, has been synthesized for the first time in this study. The results show that pentosinane is likely to be more abundant in vivo than previously appreciated. This finding represents a critical step towards understanding the role of pentosinane in human biology.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Fa-Jie Chen, Phani Mamidipalli, Venkata Reddy Sabbasani, Huaqing Liu, Yuanzhi Xia, Daesung Lee
Summary: In this study, a copper-catalyzed three-component coupling reaction was reported for the synthesis of fully substituted triazoles. Reactivities of alkyl azides and diazo compounds were controlled to enhance selectivity, particularly by introducing a ligand and adjusting stoichiometry. The use of aliphatic alkynes was crucial for achieving high selectivity and moderate to good yields.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Venkata R. Sabbasani, Hyunjin Lee, Peipei Xie, Yuanzhi Xia, Daesung Lee
CHEMISTRY-A EUROPEAN JOURNAL
(2017)
