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
Oleksii Zhelavskyi, Yin-Jia Jhang, Pavel Nagorny
Summary: This manuscript describes the transfer hydrogenation of nitrogen-containing heterocyclic compounds using immobilized chiral phosphoric acid (R)-PS-AdTRIP catalyst 3a in both batch and continuous flow systems. It was found that the enantioselectivities were significantly improved in continuous flow using a fluidized bed reactor packed with (R)-PS-AdTRIP catalyst, especially when the flow rate was increased. The optimized continuous flow conditions consistently provided higher selectivity than batch transfer hydrogenation with the same catalyst, and multiple chiral products could be generated using the same reactor.
SYNTHESIS-STUTTGART
(2023)
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
Biochemistry & Molecular Biology
Xu Li, Ting Fan, Qingji Wang, Tongfei Shi
Summary: A density functional theory study was conducted to investigate the mechanism of asymmetric transfer hydrogenation (ATH) of imines catalyzed by an indium metal-organic framework (In-MOF). The study revealed that the imine and reducing agent are simultaneously adsorbed on the chiral phosphoric acid, leading to a proton transfer reaction. The study also found that the substituent groups on the imine and the polarity of the solvent significantly affect the reaction activity and enantioselectivity.
Review
Chemistry, Physical
You-Dong Shao, Dao-Juan Cheng
Summary: Chiral phosphoric acid catalysis has witnessed significant development in the past two decades, with successful attempts in synthesizing enantioenriched axially chiral compounds through various strategies. This review highlights the advances in atropisomeric heterocycles construction enabled by chiral phosphoric acid catalysis, aiming to motivate continuous interest in atroposelective reactions.
Article
Chemistry, Applied
Shuyuan Yang, Linger Li, Junling Zhao
Summary: A chemo- and enantioselective protocol for the N-alkylation of indoles with imines using a BINOL-derived phosphoric acid catalyst was developed. The process afforded acyclic aminals of indoles with high yields and enantioselectivity. Moreover, this method showed high efficiency for the late-stage functionalization of a bioactive compound.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Baohua Cai, Yuan Cui, Jian Zhou, Yong-Bin Wang, Limin Yang, Bin Tan, Jun (Joelle) Wang
Summary: A Cu/CPA co-catalytic system was developed to achieve direct hydrophosphinylation of alkynes with phosphine oxides, delivering novel axially chiral phosphorus-containing alkenes with high yields and excellent enantioselectivities (up to 99% yield and 99% ee). DFT calculations were performed to elucidate the reaction pathway and the origin of enantiocontrol. This streamlined and modular methodology establishes a new platform for the design and application of new axially chiral styrene-phosphine ligands.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Renat Kadyrov, Oleg L. Tok
Summary: Two N-Boc-protected amino lactams were prepared from D-ornithine and D-lysine, respectively, and then converted into imido esters through O-alkylation and hydrogenated to amines under mild conditions without isolation. This approach offers a straightforward method for the synthesis of (R)-3-[(tert-butoxycarbonyl)amino]piperidine and (R)-3-[(tert-butoxycarbonyl)amino]azepane.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Multidisciplinary
Ali Shoja, Jolene P. Reid
Summary: The study shows that similar modes of activation can be invoked when substrate and catalyst features are conserved between different mechanistic regimes. A new model involving privileged noncovalent interactions is proposed to explain the enantioselectivity outcome, providing the basis for general catalyst design principles and prediction of enantioselectivity outcomes using statistical models.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Shang Gao, Meng Duan, Jiaming Liu, Peiyuan Yu, Kendall N. Houk, Ming Chen
Summary: This study presents the development of stereodivergent syntheses of enantioenriched homoallylic alcohols using a chiral nonracemic alpha-CH(2)Bpin-substituted crotylboronate. The catalyst-controlled stereoselectivity allowed for the synthesis of complementary stereoisomers of chiral homoallylic alcohols from the same boron reagent. Computational studies were conducted to investigate the origins of the observed stereoselectivity, and the resulting products are valuable for the rapid construction of polyketide structural frameworks.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Wen-Kui Yuan, Bing-Feng Shi
Summary: An unprecedented enantioselective synthesis of spiro-gamma-lactams was achieved using a simple Co-II/chiral spiro phosphoric acid binary system, resulting in high levels of enantioselectivity. Additionally, a concise synthesis of an aldose reductase inhibitor was successfully carried out under this system.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Organic
Bishnu P. Neupane, Gregory K. Friestad
Summary: Asymmetric catalysis with chiral phosphoric acids has had a significant impact in organic synthesis, transmitting stereochemical information to reactants through ion-pairing and H-bonding interactions. This mini-review highlights recent developments in the asymmetric synthesis of amines, covering various reactions.
CURRENT ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Qian-Jin An, Wang Xia, Wei-Yi Ding, Huan-Huan Liu, Shao-Hua Xiang, Yong-Bin Wang, Guofu Zhong, Bin Tan
Summary: This study presents a strategy for the synthesis of axially chiral N-arylbenzimidazoles using chiral phosphoric acid catalysis, demonstrating excellent chemo- and regioselectivity as well as high levels of enantiocontrol. The nitroso group plays a unique role in the domino reaction, acting as a linchpin to facilitate C-N bond formation and oxidative aromatization. The resulting atropisomeric products can be further elaborated to produce axially chiral derivatives for potential applications in asymmetric catalysis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Xiongfei Deng, Shiqi Zhang, Hesen Huang, Xin Cui, Zhuo Tang, Guangxun Li
Summary: Highly enantioselective sulfa-Michael additions between 2-alkenyl quinoxalines and aromatic thiols were achieved using a low loading of chiral phosphoric acid catalyst. The investigation revealed that the two C = N units of quinoxalines are essential for controlling the enantioselectivities. Substituted non-terminal 2-alkenes with aryls or alkyls, and even other electro-withdrawing groups like ketones, esters, or amides, selectively reacted and yielded the desired products with good regioselectivities, high yields, and good ee values.
CHINESE CHEMICAL LETTERS
(2023)
Article
Chemistry, Organic
Hui-Min Jiang, Jing-Hao Qin, Qing Sun, Dong Zhang, Jin-Peng Jiang, Xuan-Hui Ouyang, Ren-Jie Song, Jin-Heng Li
Summary: This article describes a copper-promoted reductive cross-coupling of nitroarenes with 4-alkyl-1,4-dihydropyridines to produce N-alkylbenzenamines. The reaction enables the construction of C(sp(3))-N bonds under oxidative conditions, providing an elegant platform for assembling N-alkylbenzenamines with good tolerance for sensitive functional groups.
ORGANIC CHEMISTRY FRONTIERS
(2022)
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)