Article
Chemistry, Organic
Ling Qi, Pei-Jun Yang, Wen-Tao Ji, Gui-De Tao, Gaosheng Yang, Zhuo Chai
Summary: In this study, we report an efficient strategy for synthesizing compounds with high pharmaceutical value using catalysts. The method is simple and feasible, with mild reaction conditions, and can be used for the synthesis of important drugs.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Medicinal
Daniel Lowicki, Piotr Przybylski
Summary: Cascade reactions are utilized by nature to construct nitrogen-containing heterocycles in a stereoselective manner, which is important in pharmacy. These heterocycles have various applications in medicine and exhibit high stereoselectivity. Domino transformations align with green chemistry principles and offer cost-effective synthesis. Cascade strategies provide novel N-heterocyclic scaffolds to optimize drug targets.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Philippe Champetter, Ismail Alahyen, Catherine Taillier, Jean-Francois Briere, Vincent Dalla, Sylvain Oudeyer, Sebastien Comesse
Summary: The study aims to compare the impact of N-alkoxy and N-alkyl moieties in domino reactions, finding that N-alkoxy exhibits higher reactivity and efficiency, leading to a wider range of products under milder conditions.
Article
Multidisciplinary Sciences
Song Xi, Jiawei Dong, Haohua Chen, Qiuyan Dong, Jiao Yang, Qiuyuan Tan, Changhui Zhang, Yu Lan, Min Zhang
Summary: The study presents a silver-catalyzed domino generation and [2,3]-sigmatropic rearrangement of ammonium ylides, leading to the stereoselective synthesis of chiral azabicycles with high enantiomeric purity (up to 99% ee). Experimental findings suggest that residual water in the reaction system plays a crucial role in facilitating the mild reaction conditions. In addition to silver salts, a stoichiometric amount of nonmetallic I-2 has also been successfully employed for the same reaction.
Article
Chemistry, Organic
Tsukasa Hirokane, Touya Kariya, Misa Takata, Kenji Matsumoto, Masahiro Yoshida
Summary: The reaction between 2-alkynylazetidines and alcohols with a gold catalyst is reported, leading to the synthesis of various substituted delta-amino-alpha,beta-unsaturated ketones through gold-promoted nucleophilic attack of alcohols followed by ring-opening of azetidine ring.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Siyang Xing, Chenyu Wang, Tingxuan Gao, Yuhan Wang, Hongzheng Wang, Hanfei Wang, Kui Wang, Bolin Zhu
Summary: A stepwise cyclization method has been developed for the synthesis of 4-spiroannulated tetrahydroisoquinoline compounds, which involves sequential ring opening of aziridines and Pictet-Spengler reaction. This strategy exhibits high bonding and cyclization efficiency, broad substrate scope, mild reaction conditions, and good generality of the ring size in the product.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Yuxuan Zhou, Siyuan Guo, Qiyuan Huang, Qiwei Lang, Gen-Qiang Chen, Xumu Zhang
Summary: A highly efficient Rh/ZhaoPhos-catalysed asymmetric hydrogenation has been developed for the synthesis of various chiral ?-butyrolactones. The reaction demonstrates excellent results with high conversion and enantioselectivity, making it a valuable method for the synthesis of diverse natural products and therapeutic substances. Further transformations using this catalytic methodology have shown promise for the efficient synthesis of enantiomerically enriched drugs.
Article
Chemistry, Multidisciplinary
Jan Sietmann, Mike Ong, Christian Mueck-Lichtenfeld, Constantin G. Daniliuc, Johannes M. Wahl
Summary: Asymmetric access to gamma-lactams was achieved using (1S,2R)-1-amino-2-indanol for chiral induction, with downstream stereoinduction up to 88:12 dr. Mechanistic analysis revealed a Curtin-Hammett scenario, supported by spectroscopic, crystallographic, and computational studies. The method allows for the synthesis of optically pure gamma-lactams, including those with all-carbon quaternary stereocenters, and is exemplified by the formal synthesis of drug molecules baclofen, brivaracetam, and pregabalin.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Dan Liu, Bin Shi, Hao Jiang, Ying Cheng, Wen-Jing Xiao, Liang-Qiu Lu
Summary: A DBU-catalyzed desymmetric [3+2] cycloaddition between para-quinamines and photogenerated ketenes was developed, yielding a variety of hydroindoles bearing all-carbon quaternary centers with good reaction efficiency and complete diastereoselectivity. This protocol features broad substrate scope, high functional group compatibility and mild reaction conditions.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Hang-Hao Li, Ya-Nan Meng, Can-Ming Chen, Yu-Qi Wang, Zhi-Xin Zhang, Zhou Xu, Bo Zhou, Long-Wu Ye
Summary: Catalytic asymmetric intermolecular [4 + 2] annulation of ynamides with para-quinone methides (p-QMs) has been achieved using a chiral Bronsted acid catalyst. This metal-free protocol represents the first catalytic asymmetric nucleophilic addition of ynamides to electrophiles and the first enantioselective annulation between p-QMs and alkynes. The methodology allows for the practical synthesis of biologically important chiral 4-aryl-3,4-dihydrocoumarins and 4-aryl-coumarins.
SCIENCE CHINA-CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Zi-Yu Zhang, Jie Ren, Ming Zhang, Xiu-Fang Xu, Xiao-Chen Wang
Summary: This study reports the synthesis of N-heterocycles using borane-catalyzed dehydrogenative cyclization of 2-cyclopropyl-N,N-dimethylanilines. The key steps include borane-mediated cyclopropane ring-opening and borane-mediated hydride abstraction from the N-methyl group. The substituent at the cyclopropyl unit greatly influences the reaction pathway and determines the major reaction product.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Debayan Roy, Beeraiah Baire
Summary: A new domino cyclative approach for the synthesis of polycyclic gamma-butenolides from beta-aryl-Z-enoate propargylic alcohols has been developed, showing potential atropisomerism and representing a novel example in organic chemistry. The synthesis process involves constructing both rings synchronously while creating a potential stereogenic rotational axis.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Jala Ranjith, Yeolib Jeong, Hyunwoo Kim, Hyun-Joon Ha
Summary: The alpha-Aziridinyl carbenium ion was observed as an intermediate for the first time in the reaction with Lewis acid BF3 center dot OEt2. This intermediate reacted selectively with various nucleophiles, including electron-rich arenes, to form stereoselective adducts as singular isomers. Spectroscopic observation and density functional theory (DFT) calculations demonstrated the origin of the stereoselectivity based on thermodynamic preference.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Paul Zebrowski, Uwe Monkowius, Mario Waser
Summary: We report a two-step approach for the enantioselective synthesis of novel chiral δ-lactams. The protocol involves an asymmetric α-allylation of activated aryl esters followed by an acid-mediated lactam formation. The method provides highly enantioselective and reasonably high-yielding products, which can be further utilized via transformations of the exocyclic double bond.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Mohamed Samir Zaky, Anne-Laure Wirotius, Olivier Coulembier, Gilles Guichard, Daniel Taton
Summary: The stereoselective ring-opening polymerization of racemic lactide was achieved using Takemoto's catalyst and a phosphazene base, resulting in highly isotactic, semi-crystalline, and metal-free polylactide.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Ranadeep Talukdar, Amrita Saha, Deo Prakash Tiwari, Manas K. Ghorai
Article
Chemistry, Organic
Masthanvali Sayyad, Imtiyaz Ahmad Wani, Deo Prakash Tiwari, Manas K. Ghorai
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Organic
Deo Prakash Tiwari, Saumya Dabral, Jian Wen, Jan Wiesenthal, Steven Terhorst, Carsten Bolm
Article
Chemistry, Organic
Jian Wen, Deo Prakash Tiwari, Carsten Bolm
Article
Chemistry, Multidisciplinary
Manas K. Ghorai, Ranadeep Talukdar, Deo Prakash Tiwari
CHEMICAL COMMUNICATIONS
(2013)
Article
Chemistry, Organic
Manas K. Ghorai, Amit Kumar, Deo Prakash Tiwari
JOURNAL OF ORGANIC CHEMISTRY
(2010)
Article
Chemistry, Organic
Manas K. Ghorai, Deo Prakash Tiwari, Nikita Jain
JOURNAL OF ORGANIC CHEMISTRY
(2013)
Article
Chemistry, Organic
Manas K. Ghorai, Deo Prakash Tiwari
JOURNAL OF ORGANIC CHEMISTRY
(2013)
Article
Chemistry, Organic
Manas K. Ghorai, Ranadeep Talukdar, Deo Prakash Tiwari
Article
Chemistry, Organic
Ranadeep Talukdar, Deo Prakash Tiwari, Amrita Saha, Manas K. Ghorai
Article
Chemistry, Organic
Steven Terhorst, Deo Prakash Tiwari, Daniela Meister, Benedict Petran, Kari Rissanen, Carsten Bolm
Article
Chemistry, Multidisciplinary
Manas K. Ghorai, Deo Prakash Tiwari, Amit Kumar, Kalpataru Das
JOURNAL OF CHEMICAL SCIENCES
(2011)
