Article
Chemistry, Organic
Subhomoy Das, Gaurav Goswami, Sandipan Halder, Manas K. Ghorai
Summary: Enolate mediated domino imino-aldol-aza-Michael and domino imino-aldol-aza-Michael-imino-aldol reactions have been developed for the diastereoselective synthesis of highly functionalized 2,6-disubstituted piperidines. The reaction mechanism involves an intermolecular imino-aldol reaction followed by an intramolecular aza-Michael reaction, depending on the presence of 1.0 or 2.0 equiv. of imine. The formation of piperidine derivatives is explained by plausible reaction mechanisms.
Article
Chemistry, Physical
Palagulla Maheswar Reddy, Kuppan Ramachandran, Pazhamalai Anbarasan
Summary: An efficient palladium-catalyzed diastereoselective synthesis of 2,2,3-trisubstituted dihydrobenzofurans has been achieved in good yield as a single diastereomer. The transformation involves in-situ generation of oxonium ylide from 2-hydroxyphenyl substituted enone and diazo compound followed by intramolecular trapping via Michael addition, leading to potent dibenzofuran derivatives in good yield.
JOURNAL OF CATALYSIS
(2021)
Article
Chemistry, Organic
Dominique E. Blackmun, Stephen A. . Chamness, Corinna S. Schindler
Summary: Azetidines are of interest in medicinal chemistry due to their favorable properties, such as increased resistance to oxidative metabolism and lower lipophilicity. The recent development of [2 + 2] reactions has expanded the methods for azetidine synthesis, but further development is needed to access more complex structures.
Article
Chemistry, Multidisciplinary
Maria Sanchez-Rosello, Marcos Escolano, Daniel Gavina, Carlos del Pozo
Summary: The asymmetric intramolecular aza-Michael reaction (IMAMR) is a convenient strategy for generating heterocycles with nitrogen-substituted stereocenters, finding widespread applications in the total synthesis of alkaloids and biologically relevant compounds. Recent developments in asymmetric versions of IMAMR mainly involve the use of organocatalysts, such as chiral imidazolidinones and diaryl prolinol derivatives. The use of N-sulfinyl imines with dual roles has also emerged as a versatile mode for performing the asymmetric IMAMR.
Article
Biochemistry & Molecular Biology
Alper Yildirim, Ufuk Atmaca, Ertan Sahin, Parham Taslimi, Tugba Taskin-Tok, Murat Celik, Ilhami Gulcin
Summary: This article examines the use of oxazolidinones in various applications such as antibiotics and protein synthesis inhibition. The synthesized compounds were found to have potent inhibitory effects on enzymes such as acetylcholinesterase and carbonic anhydrase. Molecular docking and ADMET analysis were conducted to correlate the experimental data.
JOURNAL OF BIOMOLECULAR STRUCTURE & DYNAMICS
(2023)
Article
Chemistry, Organic
Damodar Enagandhula, Raju Adepu, Prathama S. Mainkar
Summary: An efficient and diastereoselective synthesis of 1',4'-dihydro-2'H-spiro[indoline-3,3'-quinolin]-2-one derivatives was achieved using a catalytic amount of L-proline. The tandem reaction involved aza-Michael addition and aldol reaction, and proceeded under mild conditions with a broad substrate scope and excellent diastereoselectivity, providing good to excellent yields.
SYNTHESIS-STUTTGART
(2023)
Review
Chemistry, Applied
Yong-Xing Song, Da-Ming Du
Summary: The aza-Michael addition cascade reaction is an important synthetic method for constructing functionalized C-N bonds, widely used in the synthesis of chiral drugs, intermediates, and natural products. This review highlights recent developments in asymmetric synthesis, including various types of aza-Michael addition triggered cascade reactions, reaction mechanisms, and derivatization experiments.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Biochemistry & Molecular Biology
Zoran Glasovac, Luka Baresic, Davor Margetic
Summary: The reaction mechanism of guanidinium chlorides with dimethyl acetylenedicarboxylate in a aza-Michael addition reaction/intramolecular cyclization was investigated using DFT M06-2X and B3LYP computational approaches. The energies of the products were compared with experimental data or product ratios obtained from other methods. The diversity of the products was explained by the formation of different tautomers upon deprotonation. The initial nucleophilic addition was found to be the most energetically demanding step, and the overall reaction was exergonic due to methanol elimination during cyclization.
Article
Chemistry, Applied
Denisa Hidasova, Radek Pohl, Ivana Cisarova, Ullrich Jahn
Summary: The study presents an asymmetric synthesis method for N,2,3,4,5-pentasubstituted pyrrolidines through oxidative single-electron transfer-catalyzed tandem reactions, enabling the diastereodivergent single-step synthesis of pyrrolidines with four contiguous stereogenic centers by setting the configuration of two stereocenters and generating two more in a selective manner. The stereoselectivity is rationalized by a predictive model.
ADVANCED SYNTHESIS & CATALYSIS
(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
Sk Asraf Ali, Anirban Bera, Mijanur Rahaman Molla, Shubhankar Samanta
Summary: This study reports an efficient synthetic strategy using Cu(I) catalyst for the synthesis of 3-substituted N-pyridinyl isoindolinones and N-aryl substituted isoindolinones. Unexpected synthesis of N-(1H-inden-1-yl)pyridin-2-amine derivatives from the same precursors was also documented using Cu(I) catalyst.
Article
Chemistry, Physical
Jonas Elfert, Anup Bhunia, Constantin G. Daniliuc, Armido Studer
Summary: In this study, a radical transformation that enables intramolecular oxygen atom transfer to alkenes using the nitro functionality in nitroarenes as an oxygen donor is disclosed. The reaction proceeds via iron-catalyzed metal hydrogen atom transfer to alkenes and subsequent oxygenation, resulting in alkene hydration. Compared to intermolecular radical oxygenation, the intramolecular variant offers advantages, particularly in terms of diastereoselective radical hydration of conformationally flexible alkenes. The aryl moiety connecting the reactive NO2-functionality to the alkene substrate can be cleaved after oxygen transfer, yielding products derived from a formal diastereoselective intermolecular alkene hydration. Additionally, the resulting aniline entity after oxygen transfer can be used for the construction of nitrogen-containing heterocycles.
Article
Chemistry, Physical
Takuya Murai, Wenjie Lu, Toshifumi Kuribayashi, Kazuhiro Morisaki, Yoshihiro Ueda, Shohei Hamada, Yusuke Kobayashi, Takahiro Sasamori, Norihiro Tokitoh, Takeo Kawabata, Takumi Furuta
Summary: D-2-symmetric dirhodium(II) carboxylate catalysts bearing axially chiral binaphthothiophene delta-amino acid derivatives have been developed, with conformational control supported through chalcogen-bonding interactions providing well-defined and uniform asymmetric environments. These complexes act as asymmetric catalysts for stereoselective intramolecular C-H insertion to yield various cis-alpha,beta-diaryl gamma-lactones, with high diastereo- and enantioselectivities, and can also be used for short total syntheses of naturally occurring gamma-lactones.
Article
Chemistry, Organic
Susanne M. Fischer, Simon Renner, A. Daniel Boese, Christian Slugovc
Summary: Electron-rich triarylphosphines exhibit superior catalytic performance in oxa-Michael additions, especially for converting poor and intermediate Michael acceptors as well as less acidic alcohols. The affinity between the phosphines and Michael acceptors, as well as the acidity of alcohols, have significant impacts on reaction speed. Additionally, the oxidation stability of the phosphines plays a role in their performance.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Shovan Mondal, Frederic Dumur, Didier Gigmes, Mukund P. Sibi, Michele P. Bertrand, Malek Nechab
Summary: Benefiting from the increase in fundamental knowledge, there has been a continuous burst of new ideas and catalytic methods for enantioselective radical reactions in the past 20 years. This review provides a comprehensive survey of the progress achieved during this period, focusing on chiral organocatalysts and transition-metal redox catalysis. The review also discusses the merger of photocatalysis with organo- or metalla-photocatalysis and enzyme-catalyzed reactions involving radical intermediates.
Article
Biochemistry & Molecular Biology
Jungwook Kim, Hui Xiao, Junseock Koh, Yikai Wang, Jeffrey B. Bonanno, Keisha Thomas, Patricia C. Babbitt, Shoshana Brown, Young-Sam Lee, Steven C. Almo
NUCLEIC ACIDS RESEARCH
(2015)
Article
Chemistry, Medicinal
Yikai Wang, Jean-Yves Wach, Patrick Sheehan, Cheng Zhong, Chenyang Zhan, Richard Harris, Steven C. Almo, Joshua Bishop, Stephen J. Haggarty, Alexander Ramek, Kayla N. Berry, Conor O'Herin, Angela N. Koehler, Alvin W. Hung, Damian W. Young
ACS MEDICINAL CHEMISTRY LETTERS
(2016)
Article
Biochemistry & Molecular Biology
Yuan Yuan, Kate Hartland, Zarko Boskovic, Yikai Wang, Deepika Walpita, Philippe A. Lysy, Cheng Zhong, Damian W. Young, Young-kwon Kim, Nicola J. Tolliday, Etienne M. Sokal, Stuart L. Schreiber, Bridget K. Wagner
CHEMISTRY & BIOLOGY
(2013)
Correction
Biochemistry & Molecular Biology
Yuan Yuan, Kate Hartland, Zarko Boskovic, Yikai Wang, Deepika Walpita, Philippe A. Lysy, Cheng Zhong, Damian W. Young, Young-Kwon Kim, Nicola J. Tolliday, Etienne M. Sokal, Stuart L. Schreiber, Bridget K. Wagner
CHEMISTRY & BIOLOGY
(2014)
Article
Chemistry, Multidisciplinary
Yikai Wang, Miguel Jimenez, Anders S. Hansen, Eun-Ang Raiber, Stuart L. Schreiber, Damian W. Young
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2011)
Article
Chemistry, Organic
Yikai Wang, Miguel Jimenez, Patrick Sheehan, Cheng Zhong, Alvin W. Hung, Chun Pong Tam, Damian W. Young
Article
Multidisciplinary Sciences
Alvin W. Hung, Alex Ramek, Yikai Wang, Taner Kaya, J. Anthony Wilson, Paul A. Clemons, Damian W. Young
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
(2011)
Article
Chemistry, Medicinal
Chao Fang, Brendan D'Souza, Christopher F. Thompson, Matthew C. Clifton, James W. Fairman, Ben Fulroth, Alison Leed, Patrick McCarren, Lili Wang, Yikai Wang, Clementine Feau, Virendar K. Kaushik, Michelle Palmer, Guo Wei, Todd R. Golub, Brian K. Hubbard, Michael H. Serrano-Wu
ACS MEDICINAL CHEMISTRY LETTERS
(2014)
Article
Chemistry, Physical
Cheng Zhong, Yikai Wang, Conor O'Herin, Damian W. Young
Article
Chemistry, Multidisciplinary
Chong Lu, Shien Liu, Weihua Shi, Jun Yu, Zhou Zhou, Xiaoxiao Zhang, Xiaoli Lu, Faji Cai, Ning Xia, Yikai Wang
Summary: SECSE is a novel gene design platform that integrates artificial intelligence and deep learning to efficiently search and generate small molecules with potential drug activity.
JOURNAL OF CHEMINFORMATICS
(2022)
Article
Chemistry, Medicinal
Mingxing Teng, Wentao Wu, Zhixiang Li, Guangwen Yang, Jian Qin, Yikai Wang, Zhijing Hu, Haiheng Dong, Lijuan Hou, Guoping Hu, Liang Shen, Yang Zhang, Jian Li, Shuhui Chen, Jingwei Tian, Liang Ye, Jianzhao Zhang, Hongbo Wang
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2017)
Article
Chemistry, Medicinal
Yikai Wang, Zhengxia Chen, Meibi Dai, Peipei Sun, Chunqiu Wang, Yang Gao, Haixia Zhao, Wenqin Zeng, Liang Shen, Weifeng Mao, Tian Wang, Guoping Hu, Jian Li, Shuhui Chen, Chaofeng Long, Xiaoxin Chen, Junhua Liu, Yang Zhang
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2017)
Article
Chemistry, Organic
Libo Hu, Yikai Wang, Bonan Li, Da-Ming Du, Jiaxi Xu
Article
Chemistry, Organic
Bonan Li, Yikai Wang, Da-Ming Du, Jiaxi Xu
JOURNAL OF ORGANIC CHEMISTRY
(2007)
