Article
Chemistry, Multidisciplinary
Dong-Xing Zhu, Jian-Guo Liu, Ming-Hua Xu
Summary: A one-pot reaction has been developed for the stereodivergent synthesis of diverse 2,3-disubstituted dihydrobenzofurans under mild conditions with high yields and stereoselectivity. By appropriate permutations of two chiral catalysts, a wide range of chiral products can be accessed, demonstrating the ability of two chiral catalysts to independently control two contiguous stereogenic centers.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Review
Chemistry, Organic
Martina Bortolami, Francesca Leonelli, Marta Feroci, Fabrizio Vetica
Summary: Organocatalysis has been shown to be a powerful tool for the asymmetric synthesis of oxindole-based compounds, offering advantages such as step- and atom-economy, environmental friendliness, and non-toxicity.
CURRENT ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Xiao-Long Zhang, Kai-Xiang Feng, Jian-Liang Hu, Qiao-Yu Shen, Wang-Sheng Huang, Ai-Bao Xia, Chen Li, Dan-Qian Xu
Summary: An organocatalytic enantioselective quadruple-cascade reaction has been developed for the construction of fully substituted hexahydrophenanthridine, yielding tricyclic compounds with excellent diastereoselectivities and high to excellent enantioselectivities. Successful gram-scale synthesis of the tricyclic compounds containing hexahydrophenanthridine was also achieved.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Christian Ascaso-Alegre, Raquel P. Herrera, Juan Mangas-Sanchez
Summary: The combination of small-molecule catalysis and enzyme catalysis shows great potential in asymmetric synthetic chemistry. The one-pot three-step chemoenzymatic cascade combination described in this study allows for efficient synthesis of chiral nitro alcohols with high overall yields and excellent selectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Fang Xie, Yajun Sun, Hanghang Song, Jie Zhao, Zengpeng Zhang, Yue Duan, Rao Chen
Summary: The copper-catalyzed annulation of 3-aryl-2H-azirines with 2-naphthols allows for the rapid assembly of C-3-naphthol-substituted benzo[e]indoles in one pot through a cascade reaction. This method provides a new approach for the synthesis of important unreported pi-expanded naphthol/benzo[e]indole biaryls.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Poorna Chandrasekhar Settipalli, Shaik Anwar
Summary: A [2+2+2] annulation reaction between cyclohexanone, beta-nitrostyrene and 2-arylidene-1,3-indanedione has been successfully carried out to obtain multisubstituted spiro trans-decalinol derivatives at room temperature. This reaction process exhibits high chemical yields and excellent diastereoselectivity, resulting in the formation of multiple bonds and stereocenters through the Michael/nitro-Michael/Aldol process.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Applied
Claire Segovia, Jeremy Godemert, Jean-Francois Briere, Vincent Levacher, Sylvain Oudeyer
Summary: An organocatalyzed one-pot sequential deracemization of aromatic ketones with a stereogenic center at the alpha-position was achieved through an acid-base strategy, in which enantioselective protonation reaction played a key role. This protocol provides enantioenriched ketones with up to 89% ee without isolating sensitive intermediates like silyl enolates. Water was found to be crucial in this process. This one-pot sequence serves as a valuable extension to previously reported chemically driven red-ox protocols, expanding the range of molecules eligible for deracemization.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Applied
Amit Shikari, Koushik Mandal, Deepak Chopra, Subhas Chandra Pan
Summary: A new organocatalytic asymmetric synthesis method has been developed for the synthesis of cyclic acetals with a spirooxindole skeleton. It was found that a bifunctional squaramide catalyst with an adamantyl motif was the most effective in the cascade reaction, providing high diastereo- and enantioselectivities for the desired products.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Biochemistry & Molecular Biology
Dae Young Kim
Summary: A one-pot strategy has been developed for the synthesis of multisubstituted 3,4-dihydrocoumarins with high yields and excellent diastereoselectivity. This approach involves C-H oxidation and cyclization cascade reactions of 2-alkyl phenols and oxazolones in the presence of silver oxide and p-toluenesulfonic acid as catalysts.
Article
Chemistry, Multidisciplinary
Brendan Horst, Daniel S. Verdoorn, Sven Hennig, Gydo van der Heijden, Eelco Ruijter
Summary: We report a novel method for the synthesis of monoterpene indole alkaloids through an intramolecular conjugate addition/Truce-Smiles/Elcb cascade reaction. This method was successfully applied to the asymmetric total synthesis of several natural products, demonstrating its potential for the synthesis of other compounds as well.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Martina Sotolova, Martin Kamlar, Marek Remes, Pierre-Yves Geant, Ivana Cisarova, Martin Sticha, Jan Vesely
Summary: An organocatalytic asymmetric domino Michael/alpha-alkylation reaction has been developed for the synthesis of 1,2,3-trisubstituted cyclopentane carbaldehydes. The reaction, catalyzed by chiral secondary amines, exhibits high diastereo- and enantioselectivities.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Kelsey N. N. Stewart, Kendyll G. G. Hawkins, Campbell M. M. Andersen, Dylan W. W. Domaille
Summary: Dinitroalkanes can be synthesized from aliphatic aldehydes in a three-step cascade reaction catalysed by phosphate buffer and the amino acid lysine, and this methodology can be expanded to limited alcohol substrates with the inclusion of a biocatalysed alcohol oxidation. The yield of 3-(nitromethyl)hexane can be increased by staggering the introduction of the amino acid catalyst and nitromethane substrate, with near-quantitative consumption of the n-butyraldehyde intermediate. This work presents a mild synthetic method that couples multi-step catalytic cascades to generate 1,3-dinitroalkanes.
REACTION CHEMISTRY & ENGINEERING
(2023)
Article
Chemistry, Applied
Ayon Chatterjee, D. H. Sreenivasa Rao, Santosh Kumar Padhi
Summary: "In this study, a one-pot, two-step cascade reaction sequence was developed to convert benzylic alcohols to enantioenriched beta-nitroalcohols. By utilizing specific enzymes, high conversion rates and excellent stereoselectivity were achieved, demonstrating a new method for producing chiral pharmaceutical intermediates."
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Vincenzo Battaglia, Sara Meninno, Alessandra Lattanzi
Summary: In this study, a novel and concise method for the synthesis of the commonly used antiplatelet drug Plavix was developed. Through careful optimization of reaction conditions, a high synthesis yield and selectivity were achieved.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Marvin Mantel, Markus Giesler, Marian Guder, Elisabeth Ruethlein, Laura Hartmann, Joerg Pietruszka
Summary: Efficient synthesis of enantiopure key building blocks for natural product syntheses can be achieved by utilizing multiple catalytic steps within the same reaction vessel using two catalysts.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
