Article
Chemistry, Organic
Takashi Mino, Yohei Fujisawa, Shizuki Yoshida, Mitsuru Hirama, Takumu Akiyama, Ryo Saito, Yasushi Yoshida, Yoshio Kasashima, Masami Sakamoto
Summary: By synthesizing cinnamoyl amide type chiral P,olefin ligand (S)-4, separable diastereomers of 4d were obtained successfully, and asymmetric allylic substitution reactions of indoles using (S,aS)-4d as a chiral ligand demonstrated high enantioselectivities (up to 98% ee).
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Takashi Mino, Kaho Takaya, Kaito Koki, Natsume Akimoto, Yasushi Yoshida, Yoshio Kasashima, Masami Sakamoto
Summary: We synthesized N-alkyl-N-cinnamoyl amide type phosphine-olefin compounds 1 and observed axial chirality in the C(aryl)-N(amide) bond of compounds 1 using HPLC analysis with a chiral stationary phase column. Enantiomeric isomers of 1 were obtained and (-)-1 was demonstrated as a chiral ligand in Pd-catalyzed asymmetric allylic substitution reactions, leading to high enantioselectivity (up to 97% ee) in the esterification process.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Jeanne Masson-Makdissi, Liher Prieto, Xavier Abel-Snape, Mark Lautens
Summary: This study demonstrates the feasibility and advantages of combining two distinct asymmetric transition-metal-catalyzed reactions in one pot, effectively converting simple allyl enol carbonate precursors into enantioenriched cyclic ketones. Despite the challenges in controlling stereoselectivity, the products are obtained with high enantiomeric excesses exceeding 99% ee, surpassing those obtained from individual reactions. Additionally, the one-pot reaction is enantio- and diastereodivergent, allowing easy access to all stereoisomers from the same starting materials.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Xi-Jia Liu, Wen-Yun Zhang, Chao Zheng, Shu-Li You
Summary: Herein, an Ir-catalyzed asymmetric allylic substitution reaction of methyl azaarenes is reported. The reaction exhibits high yields and enantioselectivity, and utilizes the Knochel reagent for the formation of benzylic nucleophiles without additional activating reagents. The synthetic utility of this method has been demonstrated by an enantioselective synthesis of an allosteric protein kinase modulator.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Multidisciplinary Sciences
Xiang Pu, Qiu-Di Dang, Lei Yang, Xia Zhang, Dawen Niu
Summary: The authors report a doubly-stereoconvergent, Cu/Mg-catalyzed asymmetric propargylic substitution reaction that can selectively construct products with vicinal congested stereocenters. This reaction uses readily available starting materials, environmentally friendly catalysts, and has a broad substrate scope.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Jun-An Xiao, Hai Peng, Huan Zhang, Ru-Fang Meng, Chenxiang Lin, Wei Su, Yanmin Huang
Summary: The diastereoselective assembly of spiroindolenines through a synergistic scandium/gold-catalyzed dearomative spiroannulation is presented. This protocol provides access to a wide range of spiroindolenine derivatives with an average yield of 86%, exhibiting moderate to excellent diastereoselectivities (up to 97:3 dr). Experimental studies support the feasibility of bimetallic relay catalysis, and the scale-up reaction and synthetic transformations of the spiroindolenine product demonstrate its synthetic utility.
Article
Chemistry, Multidisciplinary
Gargi Nikhil Vaidya, Shyam Kumar Lokhande, Sangita Dattatray Shinde, Dinesh Parshuram Satpute, Garvita Narang, Dinesh Kumar
Summary: The first 'in-water' nickel-catalyzed chemoselective C-3-allylation of (NH)-indoles employing allylic alcohols under mild conditions is reported. The use of water not only provides sustainability but also activates allylic alcohols via hydrogen bonding and stabilizes the consequent hydroxide ion. This results in facile oxidative addition and the formation of electrophilic pi-allylNi complexes leading to C-3-allyl indoles.
Article
Chemistry, Multidisciplinary
Wei Tian, Bowen Li, Duanshuai Tian, Wenjun Tang
Summary: A palladium-catalyzed 2-alkylation of indoles with alpha-bromo esters using a P,P=O ligand has been developed. The method shows excellent regioselectivities, mild reaction conditions, and good functional group compatibility. Mechanistic studies indicate that the reaction proceeds through a radical pathway.
CHINESE CHEMICAL LETTERS
(2022)
Article
Chemistry, Physical
Prashant Kumar, Pravesh Kumar, Sugumar Venkataramani, S. S. V. Ramasastry
Summary: This study reveals a new chemical reactivity pattern of allylic gem-diacetates and successfully synthesizes complex benzo[f]chromene compounds, demonstrating the versatility of the method. Additionally, interesting photochromic properties of the new classes of benzo[f]chromenes are discovered.
Article
Chemistry, Physical
Prashant Kumar, Pravesh Kumar, Sugumar Venkataramani, S. S. V. Ramasastry
Summary: This work explores the unusual chemical reactivity pattern of allylic gem-diacetates and establishes them as new prototypes for synthesizing complex benzo[f]chromene systems. The versatility of the method in synthesizing bioactive natural products based on chromene is demonstrated, along with the discovery of interesting photochromic properties of the new classes of benzo[f]chromenes.
Article
Chemistry, Organic
Haijian Wu, Jing Gui, Manman Sun, Yongmin Ma, Jianguo Yang, Zhiming Wang
Summary: A palladium-catalyzed C-H allylation/annulation reaction was developed to synthesize 3,4-dihydroisoquinolones with a vinyl substituent. This cascade cyclization involving allylic alcohols has not been reported before. The use of commercially available allylic alcohols, water as the only by-product, and O2 as the terminal oxidant provides environmentally friendly advantages.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Chao Xia, Dong-Chao Wang, Gui-Rong Qu, Hai-Ming Guo
Summary: A highly enantioselective allylation reaction of vinylethylene carbonate by asymmetric palladium catalysis has been developed for various N-heteroaromatic substrates. The efficient synthesis of acyclic nucleoside analogs with high yields (up to 96%) and enantioselectivities (up to 99%) was demonstrated with only 0.5 mol% of Pd catalyst. Additionally, these acyclic nucleosides can undergo rapid transformation into a variety of structurally diverse chiral acyclic nucleosides and isonucleosides.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Review
Chemistry, Organic
Xinhui Yu, Ting Zhang, Jitian Liu, Xiaoxun Li
Summary: This short review summarizes recent developments in the synthesis of quaternary stereocenters via DAAA methods since 2018, showcasing its potential in organic and medicinal chemistry through representative examples of total synthesis of complex natural products.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Multidisciplinary
Ketan Kumar, Prashant Kumar, Bara Singh, Sonu Yadav, Uttam K. Mishra, Arshad J. Ansari, S. S. Ramasastry
Summary: The catalysis by transition metals is a powerful tool to access molecules with broad structural and functional diversity. Recent literature has shown the tremendous potential of transition metal-catalyzed processes in advancing organic synthesis. New conceptual advancements in palladium-catalyzed Alder-ene type cycloisomerization reactions, C-H functionalizations, and one-pot multicatalytic processes have become essential tools to access new classes of molecules.
Article
Chemistry, Organic
Qi Li, Zi-Lu Wang, Huan-Xuan Lu, Yun-He Xu
Summary: A copper-catalyzed 1,4-protosilylation of alpha-alkynyl-enones has been developed to prepare functionalized chiral homoallenylsilanes with a contiguous stereogenic center and axis, showing good yields and excellent enantioselectivities and diastereoselectivities.
Article
Chemistry, Multidisciplinary
Frederik Rainer Ehrmann, Jorna Kalim, Toni Pfaffeneder, Bruno Bernet, Christoph Hohn, Elisabeth Schaefer, Thomas Botzanowski, Sarah Cianferani, Andreas Heine, Klaus Reuter, Francois Diederich, Gerhard Klebe
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2018)
Article
Chemistry, Physical
Chen Lu, Fenglin Shen, Shuaibo Wang, Yuyang Wang, Juan Liu, Wen-Ju Bai, Xiqing Wang
Article
Chemistry, Multidisciplinary
Barry M. Trost, Wen-Ju Bai, Craig E. Stivala, Christoph Hohn, Caroline Poock, Marc Heinrich, Shiyan Xu, Jullien Rey
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2018)
Article
Chemistry, Organic
Xiu Gu, Hao Yuan, Jun Jiang, Yi Wu, Wen-Ju Bai
Article
Chemistry, Multidisciplinary
Barry M. Trost, Yu Bai, Wen-Ju Bai, Johnathan E. Schultz
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2019)
Article
Chemistry, Organic
Yang Liu, Peng Xie, Jiagen Li, Wen-Ju Bai, Jun Jiang
Article
Chemistry, Multidisciplinary
Jiayang Zhang, Yangtian Yan, Rong Hu, Ting Li, Wen-Ju Bai, Yang Yang
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Multidisciplinary
Yanxin Wei, Chen Lu, Shengsheng Jiang, Yanyan Zhang, Qiuchun Li, Wen-Ju Bai, Xiqing Wang
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Multidisciplinary
Barry M. Trost, James J. Cregg, Christoph Hohn, Wen-Ju Bai, Guoting Zhang, Jacob S. Tracy
Article
Chemistry, Medicinal
Engi Hassaan, Christoph Hohn, Frederik R. Ehrmann, F. Wieland Goetzke, Levon Movsisyan, Tobias Huefner-Wulsdorf, Maurice Sebastiani, Adrian Hartsch, Klaus Reuter, Francois Diederich, Gerhard Klebe
JOURNAL OF MEDICINAL CHEMISTRY
(2020)
Article
Chemistry, Physical
Shuaibo Wang, Shengsheng Jiang, Hao Chen, Wen-Ju Bai, Xiqing Wang
Article
Chemistry, Physical
Hao Chen, Mengfei Huang, Wenliang Yan, Wen-Ju Bai, Xiqing Wang
Summary: Directed evolution of a P450 hydroxylase leads to a highly selective engineered enzyme capable of catalyzing the oxyfunctionalization of fatty acids. This biocatalyst displays high reactivity and can convert a variety of fatty acids to optically pure beta-hydroxy fatty acids, offering a chemoenzymatic strategy to access valuable fatty acid derivatives. Molecular docking studies provide insight into the regio- and enantioselectivity of this reaction.
Article
Chemistry, Multidisciplinary
Kun Zhang, Aiqin Yu, Xuan Chu, Fudong Li, Juan Liu, Lin Liu, Wen-Ju Bai, Chao He, Xiqing Wang
Summary: Selective hydroxylation of non-activated aliphatic C-H bonds was achieved through directed evolution of P450(BS beta) hydroxylase. The reaction showed high selectivity towards various aliphatic carboxylic acids with different chain lengths, functional groups, and aromatic moieties. The X-ray structure of the evolved enzyme variant provided insights into the regio- and enantioselectivity of the reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)