Article
Chemistry, Organic
Mohamed S. H. Salem, Ankit Kumar, Makoto Sako, Tsukasa Abe, Shinobu Takizawa, Hiroaki Sasai
Summary: In this study, the disodium salt of enantiomerically pure dimeric.-cobalt(III) complex 1 was prepared and screened as a chiral catalyst for the bromocyclization of a tryptamine derivative.
Article
Chemistry, Organic
Xiao-Bao Wu, Quan Gao, Jun-Jie Fan, Zhen-Yu Zhao, Xue-Qin Tu, Hai-Qun Cao, Jie Yu
Summary: An asymmetric synthesis of 5-halomethyl pyrazolines and isoxazolines bearing a tertiary stereocenter was achieved through catalytic halocyclization of beta,gamma-unsaturated hydrazones and ketoximes. The use of Bronsted acids of anionic chiral Co(III) complexes as catalysts led to the formation of chiral compounds with high yields and enantioselectivities. Preliminary bioassay results showed that some isoxazoline derivatives exhibited significant antifungal activities.
Article
Chemistry, Multidisciplinary
Ze-Shu Wang, Lu-Jing Zhu, Cui-Ting Li, Bin-Yang Liu, Xin Hong, Long-Wu Ye
Summary: In recent years, there has been significant attention on the asymmetric catalysis of ynamides, with most reactions focused on central chirality. However, the synthesis of axially chiral compounds from ynamides has been limited to noble-metal catalysis. This study presents a metal-free protocol for the construction of axially chiral N-heterocycles from ynamides using chiral Bronsted acid-catalyzed 5-endo-dig cyclization. The method allows for the practical and atom-economical synthesis of valuable N-arylindoles with excellent enantioselectivities, and the resulting axially chiral N-arylindole skeletons can be employed in asymmetric catalysis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Xiaoxiao Song, Yanjun Fan, Zhiming Zhu, Qijian Ni
Summary: We have developed a highly straightforward strategy for the synthesis of a new axially chiral 3-arylindolizine scaffold using chiral phosphoric acid catalyst. The reaction showed good scalability and yielded a series of axially chiral 3-arylindolizines with excellent enantioselectivity. This approach not only has a broad substrate scope and mild reaction conditions, but also demonstrates the potential utility of the formed axially chiral compounds.
Article
Chemistry, Multidisciplinary
Minkyu Kim, Moon Jong Han, Hansol Lee, Paraskevi Flouda, Daria Bukharina, Kellina J. Pierce, Katarina M. Adstedt, Madeline L. Buxton, Young Hee Yoon, William T. Heller, Srikanth Singamaneni, Vladimir V. Tsukruk
Summary: In this study, a method for the synthesis of chiral metal-organic frameworks (MOFs) from achiral precursors was reported by utilizing chiral nematic cellulose-derived bio-templates. It was demonstrated that chiral MOFs, specifically zeolitic imidazolate frameworks (ZIF), can be grown from regular precursors on twisted bundles of cellulose nanocrystals, resulting in a tetragonal crystal structure with chiral space group of P4(1). The templated chiral ZIF also exhibited enantioselective recognition and chiral sensing abilities.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
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, Physical
Yin Xu, Gan-Lu Qian, Da-Qiu Cui, Peng-Cheng Qian, Chao-Yue Zhao, Xin Hong, Bo Zhou, Long-Wu Ye
Summary: Herein, a chiral Bronsted acid-catalyzed desymmetrization reaction of diynes is reported, providing a facile access to enantioenriched 1,3-diaminopropanol derivatives and γ-butyrolactones with high enantioselectivities. These products can be used as precursors for the synthesis of versatile N- and O-heterocycles, which are important structural cores of bioactive molecules. Control experiments and theoretical calculations are used to confirm the mechanism and elucidate the origin of enantioinduction.
Article
Chemistry, Organic
Alemayehu Gashaw Woldegiorgis, Zhao Han, Xufeng Lin
Summary: The highly regio-, diastereo-, and enantioselective dearomatization reaction of 1-substituted 2-naphthols and beta,gamma-alkynyl-alpha-imino esters with complete atom economy is disclosed via chiral phosphoric acid catalysis. This protocol provides facile and efficient access to asymmetric construction of axially chiral allene-derived naphthalenones bearing quaternary stereocenters in good yields with high diastereoselectivities and enantioselectivities.
Article
Chemistry, Multidisciplinary
Wei-Feng Zheng, Jingdan Chen, Xiaotian Qi, Zhongxing Huang
Summary: Stereoselective protonation is a challenge in asymmetric catalysis, but it can convert abundant acid feedstocks into structurally diverse chiral molecules. Researchers have demonstrated an anchoring group strategy to create additional catalyst-substrate interactions, allowing enantioselective decarboxylative protonation to produce alpha-amino acids. This malonate-based synthesis introduces side chains and enables the access of structurally and functionally diverse amino acids.
Article
Chemistry, Organic
Caifang Han, Xiangqing Feng, Haifeng Du
Summary: This study successfully utilized a chiral frustrated Lewis pair to achieve asymmetric halocyclization of 2-vinylbenzyl alcohols, resulting in optically active 1,3-dihydroisobenofuran derivatives with high yields. These derivatives can be conveniently converted into other useful chiral compounds.
Article
Chemistry, Multidisciplinary
Ziwei Gu, Li Zhang, Haijun Li, Shanshan Cao, Yanli Yin, Xiaowei Zhao, Xu Ban, Zhiyong Jiang
Summary: Catalytic deracemization is an ideal synthetic strategy with high atom utilization efficiency. This study presents a new platform based on photoredox-neutral catalysis for efficient enrichment of valuable analogues like alpha-amino esters through photocatalysis and chiral Bronsted acid catalysis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Yongbiao Guo, Zhenhua Gao, Junchen Li, Xiaojing Bi, Enxue Shi, Junhua Xiao
Summary: This study presents a highly efficient and practical method for the direct synthesis of 2,3-dihydroquinazolinones from diverse aldehydes with excellent yields and enantioselectivity. The method shows improved enantioselectivity for aliphatic aldehydes and wide tolerance to different functional groups. Gram-scale synthesis and simplified work-up procedure demonstrate the practicality of this method.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Shuhei Ohmura, Kei Katagiri, Haruna Kato, Takahiro Horibe, Sho Miyakawa, Jun-ya Hasegawa, Kazuaki Ishihara
Summary: The design of an ion pair consisting of a radical cation and a chiral counteranion has been shown to induce excellent enantioselectivity in various organic reactions, including [2+2] and [4+2] cycloadditions. This strategy utilizes chiral iron(III) photoredox catalysis and has the potential to expand the use of mature chiral anions for unprecedented enantioselective radical cation reactions.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Jia-Bin Pan, Zhi-Chun Yang, Xuan-Ge Zhang, Mao-Lin Li, Qi-Lin Zhou
Summary: Here, we present a method for enantioselective phosphoric acid catalyzed amination of ketenes generated from α-aryl-α-diazoketones. Mechanistic studies elucidated the reaction pathway and explained how the catalyst expedited the transformation and controlled the enantioselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Kai Matsui, Kohei Toh, Manabu Hatano, Kazuaki Ishihara
Summary: A multiselective Diels-Alder reaction involving alpha-arylacroleins and cyclopentadiene has been developed using BBr3-assisted chiral BINOL-derived phosphoric acid catalysts. The chiral cavity of the in situ-formed acid-base cooperative catalysts plays a key role in controlling the exo- and enantioselectivity, particularly by suppressing the competitive hetero Diels-Alder reaction effectively.
Article
Chemistry, Multidisciplinary
Jie Yu, Hua-Jie Jiang, Ya Zhou, Shi-Wei Luo, Liu-Zhu Gong
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2015)
Article
Chemistry, Organic
Hua-Jie Jiang, Kun Liu, Jing Wang, Na Li, Jie Yu
ORGANIC & BIOMOLECULAR CHEMISTRY
(2017)
Article
Chemistry, Organic
Na Li, Hao Yu, Rui Wang, Jia Shen, Wen-Qiang Wu, Kun Liu, Ting-Ting Sun, Zheng-Zhu Zhang, Chuan-Zhi Yao, Jie Yu
TETRAHEDRON LETTERS
(2018)
Article
Chemistry, Multidisciplinary
Hua-Jie Jiang, Xiu-Mei Zhong, Jie Yu, Ying Zhang, Xinhao Zhang, Yun-Dong Wu, Liu-Zhu Gong
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
Article
Chemistry, Organic
Rui Wang, Wen-Qiang Wu, Na Li, Jia Shen, Kun Liu, Jie Yu
Article
Chemistry, Multidisciplinary
Xue Zhang, Kun Zhao, Na Li, Jie Yu, Liu-Zhu Gong, Zhenhua Gu
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Organic
Xiao-Bao Wu, Quan Gao, Jun-Jie Fan, Zhen-Yu Zhao, Xue-Qin Tu, Hai-Qun Cao, Jie Yu
Summary: An asymmetric synthesis of 5-halomethyl pyrazolines and isoxazolines bearing a tertiary stereocenter was achieved through catalytic halocyclization of beta,gamma-unsaturated hydrazones and ketoximes. The use of Bronsted acids of anionic chiral Co(III) complexes as catalysts led to the formation of chiral compounds with high yields and enantioselectivities. Preliminary bioassay results showed that some isoxazoline derivatives exhibited significant antifungal activities.
Article
Chemistry, Multidisciplinary
Liangzhi Pang, Qilin Sun, Zhan Huang, Gen Li, Jiaojiao Liu, Jiaxu Guo, Chuanzhi Yao, Jie Yu, Qiankun Li
Summary: A palladium-catalyzed stereoselective cleavage of the C-P bond has been developed for the synthesis of atropisomers with a P-stereogenic center. The method offers high yields and high stereoselectivity, and the resulting product shows potential as a chiral catalyst in phosphine-catalyzed cycloaddition reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Multidisciplinary Sciences
Bing-Bing Sun, Kun Liu, Quan Gao, Wei Fang, Shuang Lu, Chun-Ru Wang, Chuan-Zhi Yao, Hai-Qun Cao, Jie Yu
Summary: This article reports on a strategy that enables enantioselective Ugi four-component and Ugi-azide reactions using anionic stereogenic-at-cobalt(III) complexes as catalysts. By controlling the generation and trapping of key nitrilium intermediates, highly enantioselective alpha-acylamino amides and alpha-aminotetrazoles can be obtained.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Chuan-Zhi Yao, Zu-Kui Xie, Jie-Yue Wang, Jia-Yu Zhang, Zi-Yuan Zhao, Qiankun Li, Jie Yu
Summary: Here, we present an anionic stereogenic-at-cobalt(III) complex catalysis strategy for the enantioselective halocyclization of ortho-alkynylanilines using N-halosuccinimide (NXS) as the halogen source. This method offers a distinct atroposelective approach to obtain axially chiral ortho-halo-C2-indole skeletons with excellent yields and good to high enantioselectivities (up to 99% yield, 99:1 er).
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Liangzhi Pang, Chun Wang, Congyue Ma, Jiaojiao Liu, Mengke Shi, Chuanzhi Yao, Jie Yu, Qiankun Li
Summary: In this study, P-stereogenic and axially chiral phosphinooxazoles ligands were successfully synthesized using a palladium-catalyzed method, showing high stereochemical and enantiomeric selectivities. This method has a broad substrate scope and provides an efficient way to construct new chiral molecules.
Article
Multidisciplinary Sciences
Liangzhi Pang, Zhan Huang, Qilin Sun, Gen Li, Jiaojiao Liu, Baoli Li, Congyue Ma, Jiaxu Guo, Chuanzhi Yao, Jie Yu, Qiankun Li
Summary: Chiral monodentate biaryl phosphines (MOPs) have been extensively studied as chiral ligands. The authors demonstrate a diverse synthesis method for structurally diverse MOPs containing both phosphorus and axial chirality. They employ a distinct strategy for diversity-oriented synthesis, enabled by the enantioselective cleavage of C-P bond, to create chiral Pd-II intermediates that can be transformed into enantioenriched MOPs with high diastereo- and enantioselectivities. These chiral MOPs show excellent catalytic properties in the asymmetric [3 + 2] annulation reaction, leading to the formation of chiral functionalized bicyclic imide.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Ting-Ting Sun, Kun Liu, Shun-Xin Zhang, Chun-Ru Wang, Chuan-Zhi Yao, Jie Yu
Summary: Highly enantioselective halocyclization reactions of indole derivatives, including tryptophols and tryptamines, have been achieved with anionic chiral Co(III) complexes and 1,3-dihalohydantoins (as little as 0.50 equiv). 3-Halo-fused indolines were obtained in excellent yields (up to 98%) and enantioselectivities (up to 98% ee), employing the chiral anion phase-transfer-catalysis strategy.
Review
Chemistry, Multidisciplinary
Hua-Jie Jiang, Kun Liu, Jie Yu, Ling Zhang, Liu-Zhu Gong
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2017)
