Review
Chemistry, Multidisciplinary
Rosa Lopez, Claudio Palomo
Summary: This Minireview highlights the limited but significant catalytic methods for the generation of planar chirality in strained molecules, and serves as an inspiration for the development of new unconventional procedures in the future.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Inorganic & Nuclear
Emmanuel Aubert, Abdelatif Doudouh, Emmanuel Wenger, Barbara Sechi, Paola Peluso, Patrick Pale, Victor Mamane
Summary: The design of appropriate XB chiral donor molecules is the first step towards the development of asymmetric catalysis based on halogen bond (XB). This study reports the synthesis of iodinated compounds with planar chirality and attests their XB donor property using X-ray diffraction analysis. These compounds demonstrate good catalytic properties in the aza-Diels-Alder reaction.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Hai-Yun Huang, Amal Benzai, Xinzhe Shi, Henri Doucet
Summary: Researchers are focused on developing different procedures for direct functionalization of two different C-H bonds of the same organic molecule, which is currently an important research topic in organic chemistry. Over the past decade, the number of tools to control regiodivergent C-H bond functionalizations has significantly increased.
Review
Chemistry, Multidisciplinary
Yichen Wu, Peng Wang
Summary: Optically active organosilanes have been demonstrated to be versatile chiral reagents in synthetic chemistry. Monohydrosilanes, which bear a Si-H bond, are especially unique due to their facile transformations through stereospecific bond-formation reactions. In addition, they have also been used as chiral reagents for alcohol resolution, chiral auxiliaries, mechanistic probes, and potential optoelectronic materials.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Inorganic & Nuclear
Adam J. Wright, Fiona J. McMartin, Liam G. Dyer, Lloyd H. Sayer, Philip C. Bulman Page, G. Richard Stephenson
Summary: A new copper-catalyzed desymmetrisation reaction has been successfully achieved, leading to the asymmetric synthesis of planar chiral pseudo-isocoumarins with high enantiomeric excess and yield. Tri-functionalized planar chiral ferrocenes are synthesized in a straightforward manner without the need for traditional directing group chemistry.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Mahesh S. Harariya, Romin Gogoi, Anubhav Goswami, Akhilesh K. Sharma, Garima Jindal
Summary: The mechanism of Rh2(S-NTTL)4 catalyzed carbene insertion into C(3)-H of indole is investigated using DFT methods. It is found that the enol pathway, which was previously considered to be of lower energy, can actually explain the enantioinduction. A new water-promoted mechanistic pathway involving metal-associated enol intermediate and stereochemical model is proposed to solve the conundrum. The importance of substrate-catalyst binding and water-assisted proton transfer in achieving high levels of enantioselectivity is demonstrated.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Shiyan Cheng, Qianyu Li, Xiuliang Cheng, Yu-Mei Lin, Lei Gong
Summary: This review summarizes recent progress in asymmetric reactions of alkanes and cycloalkanes, focusing on the generation of stereocenters and stereogenic centers. Elegant catalytic strategies are discussed, which enable selective recognition of C-H bonds at specific positions while maintaining high levels of stereoselectivity.
CHINESE JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Physical
Ye Lin, Tristan von Muenchow, Lutz Ackermann
Summary: 3D metallaelectro-catalyzed C-H activation is a promising strategy to obtain valuable organic molecules in an economically and environmentally friendly manner. However, achieving enantioselective C-H activation using 3D metals is challenging and has limited progress. In this study, we combined cobaltaelectro-catalyzed C-H activation with asymmetric catalysis to achieve highly enantioselective annulation of allenes, resulting in a wide range of chiral compounds with good yields and high enantioselectivities. This approach demonstrated practicality by diversifying complex bioactive compounds and drug molecules, as well as conducting large-scale enantioselective electrocatalysis in continuous flow.
Article
Chemistry, Multidisciplinary
Gongming Yang, Yi He, Tianyi Wang, Zhipeng Li, Jian Wang
Summary: In this study, a new method for the enantioselective synthesis of indole-based planar-chiral macrocycles was developed using an N-heterocyclic carbene catalyst. The method exhibited broad substrate scope, good functional group tolerance, and high yields with excellent enantioselectivities. Furthermore, the synthesized planar-chiral macrocycles offer many possibilities for the development of new catalysts, ligands, and reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Jian Zhang, Xinzhe Shi, Henri Doucet
Summary: This study explores a Pd-catalyzed annulative pi-extension reaction of 1-arylpyrroles using 1,2-dihalobenzenes as coupling partners, leading to the selective synthesis of pyrrolo[1,2-f]phenanthridines. The higher reactivity of the pyrrole C2-H bond allows for successful access to substituted pyrrolo[1,2-f]phenanthridines.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Ronghao Xie, Shixiao Chen, Yufeng Wang, Xiangcong Yin, Shuai-Shuai Li, Lubin Xu, Liang Wang
Summary: Pharmaceutically significant scaffolds of 2,3-dihydroquinolin-4-one and benzoazepine-5-one carrying a privileged 3,3'-spirocyclic oxindole moiety were successfully constructed through cascade reactions in green alcoholic media. These scaffolds have distinctive features and demonstrate various advantages.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Jun-Jie Tian, Rui-Rui Li, Gui-Xiu Tian, Xiao-Chen Wang
Summary: Here, we describe a new method for enantioselective C-H allylation of pyridines at C3 using a tandem borane and palladium catalysis. This method involves borane-catalyzed pyridine hydroboration, palladium-catalyzed enantioselective allylation of the resulting dihydropyridines with allylic esters, and air oxidation to afford the products. This method allows for the introduction of an allylic group at C3 with excellent regio- and enantioselectivities.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Hui Yang, Ru Zhang, Su-Zhen Zhang, Qing Gu, Shu-Li You
Summary: Researchers have developed a series of chiral spiro ligands (BCSCp) from commercially available and cheap Bisphenol C, and prepared their corresponding rhodium complexes. These complexes have been successfully applied in enantioselective aryl C-H addition to nitroalkenes, producing C-H adducts with yields up to 88% and ee up to 98%.
Article
Chemistry, Multidisciplinary
Kristina Plevova, Peter Kisszekelyi, Denisa Vargova, Samuel Andrejcak, Viktor Toth, LukaS Fertal, Erik Rakovsky, Juraj Filo, Radovan Sebesta
Summary: This study demonstrates the diastereoselective double C-H heteroarylation of chiral ferrocenes using Pd-complexes with chiral mono-protected amino acids, resulting in a variety of functionalized compounds. The absolute configurations of CH-activation products were confirmed using X-ray crystallographic analysis and CD spectroscopy, while insights into the reaction mechanism and stereoinduction were provided by F-19 NMR kinetic study and DFT calculations.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Ziyong Li, Ying Chen, Chuang Wang, Guangyang Xu, Ying Shao, Xinhao Zhang, Shengbiao Tang, Jiangtao Sun
Summary: The atroposelective synthesis of biaryl atropisomers via asymmetric C(sp(2))-H bond insertion reaction of arenes under rhodium catalysis has been achieved, providing moderate to excellent yields with good enantiomeric ratios. Further investigation suggests that this type of axially biaryl scaffold may have promising potentials in developing novel chiral ligands.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
