Review
Chemistry, Multidisciplinary
Mu-Wang Chen, Bo Wu, Zheng Liu, Yong-Gui Zhou
Summary: This Account summarizes our endeavors in rational design, synthesis, regeneration, and application of the NAD(P)H models. The regenerable achiral and chiral coenzyme NAD(P)H models were successfully applied to biomimetic asymmetric reduction reactions. The detailed mechanism of the reaction was elucidated through a combination of experiments and density functional theory calculations.
ACCOUNTS OF CHEMICAL RESEARCH
(2023)
Review
Chemistry, Organic
Adam Mark Palvolgyi, Fabian Scharinger, Michael Schnuerch, Katharina Bica-Schroeder
Summary: Chiral phosphoric acid catalysts show high activity and enantioselectivity in organocatalytic asymmetric transfer hydrogenation, with promising development prospects. These catalysts are widely used in asymmetric reduction reactions of various compounds, and are increasingly applied in multicomponent/cascade reactions, demonstrating significant synthetic potential.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Jiufeng Wu, Claire M. Young, Andrew D. Smith
Summary: A new protocol has been developed for the isothiourea-catalysed transfer hydrogenation of alpha,beta-unsaturated para-nitrophenyl esters using Hantzsch ester. Good to excellent yields were observed, especially with alpha,beta-unsaturated aryl esters bearing electron-withdrawing beta-substituents. The aryl ester products can be isolated directly in moderate to excellent yields or converted to methyl esters or benzyl amides after in situ reaction with the appropriate nucleophile. Preliminary experiments showed modest enantioinduction when a chiral isothiourea catalyst was used.
Article
Chemistry, Organic
Aitor Maestro, Bence S. Nagy, Sandor B. Oetvoes, C. Oliver Kappe
Summary: A telescoped continuous flow process for the enantioselective synthesis of chiral precursors of 1-aryl-1,3-diols is reported. The process is stable and represents a transition-metal free approach to asymmetric synthesis.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Chendan Zhu, Francesca Mandrelli, Hui Zhou, Rajat Maji, Benjamin List
Summary: A scalable catalytic approach for enantiopure and unmodified beta(2)-amino acids was developed, utilizing a confined imidodiphosphorimidate (IDPi) catalyst and a silylated aminomethyl ether. Both aromatic and aliphatic beta(2)-amino acids can be obtained in high yields, purity, and enantioselectivity. Mechanistic studies suggest the reaction proceeds via silylium-based asymmetric counteranion-directed catalysis (Si-ACDC) with a proposed transition state for explaining enantioselectivity based on density functional theory calculations.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Biochemistry & Molecular Biology
Si-Jia Liu, Man-Su Tu, Kai-Yue Liu, Jia-Yi Chen, Shao-Fei Ni, Yu-Chen Zhang, Feng Shi
Summary: The catalytic asymmetric [2 + 4] cycloadditions of 3-vinylindoles with ortho-quinone methides using chiral phosphoric acid as the catalyst resulted in a series of indole-containing chroman derivatives with high structural diversity, overall high yields (up to 98%), good diastereoselectivities (up to 93:7 dr), and moderate to excellent enantioselectivities (up to 98% ee).
Article
Chemistry, Multidisciplinary
Avene C. Colgan, Rupert S. J. Proctor, David C. Gibson, Padon Chuentragool, Antti S. K. Lahdenpera, Kristaps Ermanis, Robert J. Phipps
Summary: This study reports a significant advancement in the catalytic enantioselective Minisci reaction, allowing the use of α-hydroxy radical coupling partners to obtain valuable enantioenriched secondary alcohol products. The approach is highly regioselective as well as highly enantioselective.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Ke-Wei Chen, Zhi-Han Chen, Shuang Yang, Shu-Fang Wu, Yu-Chen Zhang, Feng Shi
Summary: A new strategy has been developed for the highly atroposelective synthesis of N-N axially chiral indole scaffolds and bispyrroles, which can be used as chiral organocatalysts and exhibit potent anticancer activity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Xin-Qian Liu, Yang Guo, Wen-Qin Yu, Biquan Xiong, Peng-Fei Huang, Ke-Wen Tang, Yu Liu
Summary: This article describes a visible-light-induced three-component reaction of 2-arylindoles/benzimidazoles, Hantzsch esters, and sodium pyrosulfite for the synthesis of alkylsulfonatedisoquinolinones. Hantzsch esters and Na2S2O5 act as alkyl radical precursors and SO2 surrogate, respectively. This method exhibits good functional group tolerance and substrate applicability under mild conditions.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Organic
Megha Balha, Chandrakanta Parida, Subhas Chandra Pan
Summary: This review article summarizes the recent developments in organocatalytic asymmetric ene reactions, which are important methods for the formation of C-C bonds in organic synthesis. The article highlights the thorough study and various catalytic asymmetric reports published since Kurt Alder's development of ene reactions in 1943.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Meng Duan, Christian David Diaz-Oviedo, Yang Zhou, Xiangyang Chen, Peiyuan Yu, Benjamin List, Kendall N. Houk, Yu Lan
Summary: Computations and experiments were conducted to develop new chiral phosphoric acids for epoxide thionations. It was found that bulky ortho-substituents on the CPA's 3,3'-aryl groups are crucial for restricting the epoxide position in key transition states for enantioselectivity-determining steps. Larger para-substituents significantly improve the enantioselectivity of the reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Zhou-Hao Zhu, Yi-Xuan Ding, Bo Wu, Yong-Gui Zhou
Summary: The asymmetric reduction of tetrasubstituted olefins has seen significant development, leading to an urgent demand for an effective method. By mimicking the coenzyme NAD(P)H, researchers have successfully reduced 2,3-substituted 1H-inden-1-ones using the catalytic chiral NAD(P)H model CYNAM, achieving high yields (up to 98%) and good enantioselectivity (up to 99% ee). The reduced product can also be efficiently used for the concise synthesis of chiral bioactive molecules.
Article
Chemistry, Organic
Renat Kadyrov
Summary: This study demonstrates the reduction of carboxylic ortho esters to acetals using hydrogen as the reducing agent. The reaction was carried out under mild conditions using commercially available hydrogenation catalysts (5% Pd/C and 5% Pt/C). The method is particularly useful for the selective transformation of carboxylic acids and lactones into acetals.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Applied
David L. Hughes
Summary: This review examines the contributions of asymmetric organocatalysis in patent literature since 2018, focusing on reactions catalyzed by Cinchona alkaloids, phosphonium salts, proline-derived catalysts, and chiral phosphoric acids. It also highlights examples of using asymmetric organocatalysis in the industrial preparation of pharmaceutical intermediates.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2022)
Article
Chemistry, Applied
Yongkai Pan, Qianwen Jiang, Subramani Rajkumar, Chaofan Zhu, Jinglei Xie, Shaoze Yu, Yunrong Chen, Yu-Peng He, Xiaoyu Yang
Summary: A series of cyclohexyl-fused SPINOL-derived phosphoric acids have been developed for the kinetic resolution of 2-N-acylamido tertiary allylic alcohols, providing access to chiral oxazolines with high enantioselectivities. Gram-scale reactions with 1 mol% catalyst loading and transformations of the chiral products demonstrate the value of these methods.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Thanh Binh Nguyen, Pascal Retailleau
Article
Chemistry, Organic
Thanh Binh Nguyen, Le Anh Nguyen, Mathilde Corbin, Pascal Retailleau, Ludmila Ermolenko, Ali Al-Mourabit
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Organic
Thanh Binh Nguyen, Pascal Retailleau
Article
Chemistry, Applied
Thanh Binh Nguyen, Le Phuong Anh Nguyen, Thi Thu Tram Nguyen
ADVANCED SYNTHESIS & CATALYSIS
(2019)
Article
Chemistry, Applied
Thanh Binh Nguyen, Jing-ya Hou, Pascal Retailleau
ADVANCED SYNTHESIS & CATALYSIS
(2019)
Article
Chemistry, Applied
Thanh Binh Nguyen, Pascal Retailleau
ADVANCED SYNTHESIS & CATALYSIS
(2019)
Article
Chemistry, Applied
Le Anh Nguyen, Pascal Retailleau, Thanh Binh Nguyen
ADVANCED SYNTHESIS & CATALYSIS
(2019)
Article
Chemistry, Organic
Thanh Binh Nguyen, Pascal Retailleau
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Organic
Thanh Binh Nguyen, Le Anh Nguyen, Pascal Retailleau
Article
Chemistry, Applied
Thi Thu Tram Nguyen, Van Anh Le, Pascal Retailleau, Thanh Binh Nguyen
ADVANCED SYNTHESIS & CATALYSIS
(2020)
Article
Chemistry, Multidisciplinary
Thanh Binh Nguyen, Tuan Minh Nguyen, Pascal Retailleau
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Article
Chemistry, Organic
Le Anh Nguyen, Thai Duy Dang, Quoc Anh Ngo, Binh Thanh Nguyen
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Applied
Thanh Binh Nguyen, Pascal Retailleau
ADVANCED SYNTHESIS & CATALYSIS
(2020)
Review
Chemistry, Applied
Thanh Binh Nguyen
ADVANCED SYNTHESIS & CATALYSIS
(2020)
Article
Chemistry, Organic
Amr El-Demerdash, Ludmila Ermolenko, Emmanuelle Gros, Pascal Retailleau, Binh Nguyen Thanh, Anne Gauvin-Bialecki, Ali Al-Mourabit
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2020)