Article
Chemistry, Organic
Xi Gao, Chengwen Li, Li Chen, Xin Li
Summary: A highly enantioselective arylation reaction of 3-aryl-5-aminopyrazoles and quinone derivatives was achieved using a chiral phosphoric acid catalyst under mild conditions. The reaction showed a broad scope in terms of both arylation reaction partners and produced axially chiral arylpyrazoles with high yields (up to 95%) and enantioselectivity (99%). The reaction was proven to be efficient, as the catalyst loadings could be reduced to 1 mol % while maintaining enantioselectivity. Moreover, the synthetic utility of the protocol was demonstrated through gram-scale reaction and product transformation.
Article
Chemistry, Multidisciplinary
Yuling Wu, Wu-Jingyun Zhou, Laiping Yao, Yadi Niu, Hongli Zhao, Cheng Peng, Bo Han, Wei Huang, Gu Zhan
Summary: In this study, an organocatalytic strategy for coupling aryl-naphthoquinones with thiosugars is reported, leading to the synthesis of axially chiral naphthoquinone thioglycoside with excellent stereoselectivity. Mechanistic studies showed the crucial role of H-bonding in stereochemical recognition. The reaction pathway involves atroposelective addition, followed by stereoretentive oxidation of the hydroquinone intermediate.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Kazutaka Shibatomi
Summary: This paper summarizes our recent efforts in the enantioselective organocatalytic synthesis of chiral halogenated compounds. The discussion includes enantioselective alpha-halogenation of aldehydes, decarboxylative chlorination of beta-keto acids, and enantioselective C-C bond formation at the trifluoromethylated prochiral carbon to yield organohalides with chlorinated, fluorinated, or trifluoromethylated chiral stereogenic centers. Common organocatalysts such as Jorgensen-Hayashi catalyst and cinchona alkaloid-derivatived catalyst were applied, and novel chiral amine catalysts were developed for these reactions. Stereospecific derivatizations of the chiral halogenated compounds via nucleophilic substitution are also discussed, resulting in the synthesis of many novel chiral compounds that have not been reported before, even as racemates.
Article
Chemistry, Multidisciplinary
Ruslan A. Kovalevsky, Alexander S. Kucherenko, Sergei G. Zlotin
Summary: A bifunctional tertiary amine-squaramide-catalyzed enantioselective Mannich-type addition reaction was developed for the synthesis of non-proteinogenic alpha-amino acids and their derivatives. The resulting adducts can be easily transformed into target compounds through oxidative fragmentation, esterification, amidation, and deprotection reactions. The absolute configuration of the products was confirmed by comparing the optical rotation data.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Ji-Wei Ren, Zhen-Zhen Xie, Lan Zheng, Zhi-Peng Ye, Zhi-Xiong Deng, Qing-Lan Zhao, Jun-An Xiao, Kai Chen, Hao-Yue Xiang, Xiao-Qing Chen, Hua Yang
Summary: In this work, an organocatalytic enantioselective ring-reorganization domino sequence was established for the synthesis of pyrrolo[3,4-c]quinolinones with multiple chiral centers. The reaction showed high yields, excellent diastereoselectivities, and high enantioselectivities.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Chandrakanta Parida, Buddhadeb Mondal, Animesh Ghosh, Subhas Chandra Pan
Summary: A novel organocatalytic asymmetric synthesis method for spirooxindole embedded oxazolidines has been developed using a specific catalyst, resulting in good diastereoselectivity and high enantioselectivity of the products.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Tom D. D'Arcy, Mark R. J. Elsegood, Benjamin R. Buckley
Summary: The highly enantioselective organocatalytic tandem o-HPD-[4+2] reaction described offers a practical method for the synthesis of complex scaffolds. This approach utilizes a chiral oxaziridinium organocatalyst to afford dearomatized products in high enantioselectivity, demonstrating its potential for gram-scale applications.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Pavan Sudheer Akula, Yung-Ju Wang, Bor-Cherng Hong, Gene-Hsiang Lee, Su-Ying Chien
Summary: The organocatalytic alpha-alkylation of vinylogous carbonyl compounds to hydroxynitroolefins for the synthesis of hemiacetals was achieved with excellent enantioselectivities and high yields. The addition of Et3N led to high diastereoselectivity (>20:1). The alpha- and gamma-alkylation of vinylogous ketone against nitroolefins exhibited high but opposite facial selectivities, with the transformation of the hemiacetal products demonstrated to other polycyclic compounds, including the euroticin B analog.
Article
Multidisciplinary Sciences
Hui Zhou, Yu Zhou, Han Yong Bae, Markus Leutzsch, Yihang Li, Chandra Kanta De, Gui-Juan Cheng, Benjamin List
Summary: Enzymatic stereoselectivity is often better than most chemical catalysts in the conversion of small substrates. A recent study has reported the development of broadly applicable confined organocatalysts for the highly enantioselective cyanosilylation reaction. The selectivity (98:2 enantiomeric ratio) of the catalyst towards the pharmaceutically relevant product exceeds any other catalyst class, including engineered biocatalysts.
Article
Chemistry, Organic
Ankit Yadav, Mamta Gill, Vinod K. Singh
Summary: The asymmetric synthesis of an unprecedented exocyclic dihydronaphthalene and an axially chiral naphthalene chalcone has been reported. Good to excellent asymmetric induction is achieved through the unusual formation of exocyclic dihydronaphthalene, which is crucial for ensuring axial chirality. This is the first report of exocyclic molecules enabling the synthesis of axially chiral chalcones via stepwise asymmetric vinylogous domino double-isomerization using secondary amine catalysis.
Article
Chemistry, Multidisciplinary
Cong-Shuai Wang, Qi Xiong, Hui Xu, Hao-Ran Yang, Yanfeng Dang, Xiu-Qin Dong, Chun-Jiang Wang
Summary: A novel organocatalytic method for the synthesis of axially chiral N,N'-pyrrolylindoles based on o-alkynylanilines has been successfully developed using chiral phosphoric acid as the catalyst. This strategy allows for the efficient and selective synthesis of N,N'-pyrrolylindoles with excellent yields and enantioselectivity. Preliminary biological activity studies show that these compounds exhibit promising cytotoxicity against various cancer cell lines.
Article
Chemistry, Multidisciplinary
Michael J. Tilby, Damien F. Dewez, Adrian Hall, Carolina Martinez Lamenca, Michael C. Willis
Summary: In this study, the absolute configuration of sulfur-stereogenic aza-sulfur derivatives was determined using a unique feature of sulfonimidamides. Enantioselective alkylation was achieved by generating prochiral ions from sulfonimidamides with the help of a bis-quaternized phase-transfer catalyst. This demonstrates the potential of using configurationally labile aza-sulfur species in asymmetric catalysis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Multidisciplinary Sciences
Prithwish Goswami, Sung Yeon Cho, Jin Hyun Park, Woo Hee Kim, Hyun Jin Kim, Myoung Hyeon Shin, Han Yong Bae
Summary: This study presents an efficient water-accelerated organocatalytic method for the synthesis of α-tertiary amines incorporating homoallylic amine structures using ketones as starting material. The developed method is mild, applicable to various substrates, and scalable.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Sumi Joseph, Qui-Nhi Duong, Lukas Schifferer, Olga Garcia Manchen
Summary: An enantioselective anion-binding catalyzed allylation method has been developed for the rapid synthesis of chiral α-allyl dihydroquinolines. Using a tetrakis-triazole-based hydrogen-bond donor catalyst, these chiral N-heterocycles were obtained in good yields (up to 90%) and with high enantioselectivity (up to 89:11 e. r.). Moreover, the versatility of the allyl moiety in the products was demonstrated through selective post-epoxidation and aziridination reactions, resulting in highly decorated chiral molecules with up to four stereocenters and high enantioselectivity (up to 94:6 e. r.).
Review
Chemistry, Multidisciplinary
Diksha Gambhir, Sanjay Singh, Ravi P. Singh
Summary: The rational combination of two catalysts has been widely used in the synthesis of biologically and pharmacologically relevant chiral compounds. This review article focuses on the achievements in asymmetric catalysis and synthesis using enamine and iminium-based dual organocatalytic systems. The combination of enamine/iminium catalysis with other organocatalytic systems has paved the way for the construction of complex chiral compounds.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Chia-Jui Lee, Cheng-Che Tsai, Shao-Hao Hong, Geng-Hua Chang, Mei-Chun Yang, Lennart Moehlmann, Wenwei Lin
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2015)
Article
Chemistry, Organic
Chi-Han Chen, Chi-Ting Ko, Ganapuram Madhusudhan Reddy, Chia-Jui Lee, Wenwei Lin
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2015)
Article
Chemistry, Organic
Yeong-Jiunn Jang, Yu-Shan Chen, Chia-Jui Lee, Chi-Han Chen, Ganapuram Madhusudhan Reddy, Chi-Ting Ko, Wenwei Lin
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2015)
Article
Chemistry, Organic
Yi-Ru Chen, Utpal Das, Meng-Hsien Liu, Wenwei Lin
JOURNAL OF ORGANIC CHEMISTRY
(2015)
Article
Chemistry, Organic
Geng-Hua Chang, Chein-Yi Wang, G. Madhusudhan Reddy, Yi-Ling Tsai, Wenwei Lin
JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Organic
Shu-Mei Yang, Ganapuram Madhusudhan Reddy, Meng-Hsien Liu, Tzu-Ping Wang, Jhen-Kuei Yu, Wenwei Lin
JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Organic
G. Madhusudhan Reddy, Chi-Ting Ko, Kai-Hong Hsieh, Chia-Jui Lee, Utpal Das, Wenwei Lin
JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Organic
Lennart Moehlmann, Geng-Hua Chang, G. Madhusudhan Reddy, Chia-Jui Lee, Wenwei Lin
Article
Chemistry, Organic
Chia-Jui Lee, Tzu-Hsiu Chang, Jhen-Kuei Yu, Ganapuram Madhusudhan Reddy, Ming-Yu Hsiao, Wenwei Lin
Article
Chemistry, Organic
Shu-Mei Yang, Yi-Ling Tsai, Ganapuram Madhusudhan Reddy, Lennart Mohlmann, Wenwei Lin
JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Multidisciplinary
Shu-Mei Yang, Chein-Yi Wang, Chun-Kai Lin, Praneeth Karanam, Ganapuram Madhusudhan Reddy, Yi-Ling Tsai, Wenwei Lin
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2018)
Article
Chemistry, Organic
Praneeth Karanam, Ganapuram Madhusudhan Reddy, Srinivasa Rao Koppolu, Wenwei Lin
TETRAHEDRON LETTERS
(2018)
Article
Chemistry, Multidisciplinary
Jhen-Kuei Yu, Han-Wei Chien, Yi-Jung Lin, Praneeth Karanam, Yu-Heng Chen, Wenwei Lin
CHEMICAL COMMUNICATIONS
(2018)
Article
Chemistry, Multidisciplinary
Shu-Mei Yang, Ganapuram Madhusudhan Reddy, Tzu-Ping Wang, Yu-Sheng Yeh, Min Wang, Wenwei Lin
CHEMICAL COMMUNICATIONS
(2017)
Article
Chemistry, Multidisciplinary
Yi-Ru Chen, Ganapuram Madhusudhan Reddy, Shao-Hao Hong, Ying-Zheng Wang, Jhen-Kuei Yu, Wenwei Lin
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2017)
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)