Article
Chemistry, Multidisciplinary
Ning Li, Wenjing Lu, Weizhi Gu, Kuiliang Li, Jindong Li, Yangmian Lu, Zhenggen Zha, Zhiyong Wang
Summary: An asymmetric Michael/hemiketalization reaction was developed between isatin-derived beta, gamma-unsaturated alpha-ketoesters and 4-hydroxycoumarins in aqueous media. A series of chiral spirooxindole derivatives with an all-carbon quaternary stereogenic center were obtained in high yields (up to 93%) and excellent enantioselectivities (up to 98%).
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Jin Jiaping, Alemayehu Gashaw Woldegiorgis, Xufeng Lin
Summary: Here, we report an enantioselective protocol for the chiral phosphoric acid-catalyzed addition of 3-arylisoxazol-5-amines to highly reactive 3-methide-3H-pyrroles. This protocol provides a diverse range of heterotriarylmethanes bearing an amino acid moiety in good yields (up to 97%) and high enantioselectivities (up to 93% ee) under mild conditions. The utilization of a chiral spirocyclic phosphoric acid is crucial in converting the initial 1H-pyrrol-3-yl carbinols into reactive 3-methide-3H-pyrroles and achieving the desired enantioselective transformation.
Article
Chemistry, Organic
Esra Dundar, Cihangir Tanyeli
Summary: A series of chiral bifunctional squaramide organocatalysts were evaluated for their application in Friedel-Crafts alkylation of indoles, showing high enantioselectivity and moderate yields. This new asymmetric transformation provides a simple, efficient, clean, and environmentally friendly route for chemical synthesis.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Organic
Zeynep Dilsad Susam, Bilge Deniz Ozcan, Enis Kurtkaya, Erol Yildirim, Cihangir Tanyeli
Summary: In this study, bifunctional quinine-derived organocatalysts were used to catalyze the asymmetric Friedel-Crafts/S(N)2 domino reaction, resulting in enantiomerically enriched products. Density functional theory calculations were also performed to explain the stereoselectivity of the products.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Kosuke Nakashima, Sumire Hanamura, Aoi Imamura, Yasuyuki Matsushima, Shin-ichi Hirashima, Tsuyoshi Miura
Summary: This study investigates the asymmetric Friedel-Crafts alkylation of indoles with alpha,beta-unsaturated trifluoromethyl ketones using a squaramide organocatalyst. The squaramide organocatalyst efficiently promotes the reaction, yielding products with both indole motif and trifluoromethyl group in high yields and excellent enantioselectivities (up to 99% ee). The transformation of the obtained adduct to a chiral spiro indoline 3-one is also demonstrated.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Yunlong Zhao, Rou Xiao, Weibin Fang, Junling Zhao
Summary: This study presents a protocol for the highly selective addition reaction of isatin-derived beta,gamma-unsaturated alpha-ketoesters with 4-aminoindoles at the C7 position. The reaction, catalyzed by a SPINOL-derived chiral phosphoric acid, yields bisindole derivatives with up to 97% enantiomeric excess. Further biological testing revealed that the products have high cytotoxicity against various cancer cell lines.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Takanori Shibata, Mio Sasaki, Masafumi Kojima, Mamoru Ito
Summary: The chiral Ir(I)-catalyzed intermolecular reaction of N-carbamoylpyrrole and indole derivatives with alpha,beta-unsaturated carbonyl compounds proceeded with high enantioselectivity, yielding chirally functionalized pyrroles and indoles as formal C-H conjugate adducts. The reaction mechanism was further investigated through deuterium labeling experiments.
Article
Chemistry, Multidisciplinary
Qian-Yi Wang, Teng-Fei Liu, Li-Feng Chu, Yun Yao, Chong-Dao Lu
Summary: In the presence of a chiral spiro phosphoric acid catalyst, the asymmetric reaction of disubstituted ketenes with N-H pyrroles occurred to afford enantioenriched C-acylated pyrroles bearing alpha-stereogenic carbon centres. This reaction represents a rare example of catalytic asymmetric reaction of ketenes with carbon-based nucleophiles, with significant research implications.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Velu Saravanan, Arasambattu K. Mohanakrishnan
Summary: A one-pot synthesis of aryl- and heteroaryl-annulated carbazoles was achieved from 2/3-bromomethylindoles, along with a bis-domino reaction of 2,5-bis(bromomethyl)pyrrole with selected heteroarenes. The synthesized thienocarbazoles and thienodibenzofurans were successfully utilized for a second-generation domino reaction.
SYNTHESIS-STUTTGART
(2021)
Article
Biochemistry & Molecular Biology
Mohammad Shahidul Islam, Abdullah Saleh Alammari, Assem Barakat, Saeed Alshahrani, Matti Haukka, Abdullah Mohammed Al-Majid
Summary: Five new C-2-symmetric chiral ligands were synthesized from enantiopure amino alcohols, and used for Friedel-Crafts asymmetric alkylation. The bis(oxazolinyl)thiophene ligands showed higher efficiency in inducing asymmetric alkylation compared to bis(imidazolinyl)thiophene analogues.
Article
Chemistry, Organic
Cheng Huang, Zhifei Zhao, Shiwu Li, Jixing Zhao, Leifang Wu, Chengzhi Gu
Summary: A highly enantioselective conjugate addition has been developed for the reaction between indolizine and its analogues with alpha,beta-unsaturated 2-acyl imidazoles. This method provides excellent yields and enantioselectivities, overcoming the limitations of organocatalysts in controlling stereoselectivity.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Jeanne Masson-Makdissi, Liher Prieto, Xavier Abel-Snape, Mark Lautens
Summary: This study demonstrates the feasibility and advantages of combining two distinct asymmetric transition-metal-catalyzed reactions in one pot, effectively converting simple allyl enol carbonate precursors into enantioenriched cyclic ketones. Despite the challenges in controlling stereoselectivity, the products are obtained with high enantiomeric excesses exceeding 99% ee, surpassing those obtained from individual reactions. Additionally, the one-pot reaction is enantio- and diastereodivergent, allowing easy access to all stereoisomers from the same starting materials.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Yuki Saito, Shu Kobayashi
Summary: The article discusses the application of chiral heterogeneous Sc catalysts in continuous-flow reactions, achieving efficient synthesis of compounds through noncovalent interactions and the crucial role of heteropoly acid.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Takashi Mino, Yohei Fujisawa, Shizuki Yoshida, Mitsuru Hirama, Takumu Akiyama, Ryo Saito, Yasushi Yoshida, Yoshio Kasashima, Masami Sakamoto
Summary: By synthesizing cinnamoyl amide type chiral P,olefin ligand (S)-4, separable diastereomers of 4d were obtained successfully, and asymmetric allylic substitution reactions of indoles using (S,aS)-4d as a chiral ligand demonstrated high enantioselectivities (up to 98% ee).
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Eri Ogino, Ayu Nakamura, Satoru Kuwano, Takayoshi Arai
Summary: AMB4 is an efficient organocatalyst for the asymmetric epoxidation of various alkylidenemalononitriles, leading to the formation of chiral dihydroquinoxalinyl spirooxindoles from isatilidenemalononitriles.
Article
Chemistry, Inorganic & Nuclear
Jun-Qi Zhang, Yunkui Liu, Xing-Wang Wang, Liming Zhang
Article
Chemistry, Organic
Jia-Ming Hu, Jun-Qi Zhang, Bing-Bing Sun, Jun-Bo Chen, Jie-Qiang Yu, Xiao-Peng Yang, Hao-Peng Lv, Zheng Wang, Xing-Wang Wang
Article
Chemistry, Physical
Jun-Bo Chen, Man Xu, Jun-Qi Zhang, Bing-Bing Sun, Jia-Ming Hu, Jie-Qiang Yu, Xing-Wang Wang, Yuanzhi Xia, Zheng Wang
Article
Chemistry, Organic
Wei-Tai Fan, Xiao-Peng Yang, Hao-Peng Lv, Xing-Wang Wang, Zheng Wang
Article
Chemistry, Organic
Hao-Peng Lv, Xiao-Peng Yang, Bai-Lin Wang, Hao-Di Yang, Xing-Wang Wang, Zheng Wang
Summary: An asymmetric [3 + 2] cycloaddition reaction has been developed for the synthesis of chiral multistereogenic vinyltetrahydrofurans using the Pd complex of a bidentate phosphoramidite (Me-BIPAM) as the catalyst. The reaction provides a wide variety of products in good yields with excellent diastereo- and enantioselectivities (up to >20:1 dr, 99% ee).
Article
Chemistry, Applied
Hao-Di Yang, Jun-Bo Chen, Cheng Peng, Wen-Kai Liu, Sheng-Suo Zhou, Jia-Xin Song, Zheng-Hang Qi, Yong Wang, Xing-Wang Wang
Summary: Chiral bis-oxalamide/rare-earth metal complexes catalyze the asymmetric inverse-electron-demand oxa-hetero-Diels-Alder reactions. The reactions produce optically active functionalized dihydropyran compounds with high diastereo- and enantioselectivity. The coordination mode of chiral bis-oxalamide with Sc(III) and the regio- and stereocontrol were investigated.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Wen-Kai Liu, Bai-Lin Wang, Sheng-Suo Zhou, Jun-Hao Shen, Zheng Wang, Xing-Wang Wang
Summary: An asymmetric linear selective allylic alkylation of vinylaziridines with 3-aryl oxindoles has been achieved using a chiral oxamide-phosphine/palladium complex in methanol. This reaction provides a wide range of 3,3-disubstituted oxindole derivatives with excellent regio- and enantioselectivities.
Article
Chemistry, Applied
Jun-Hao Shen, Sheng-Suo Zhou, Bai-Lin Wang, Wen-Kai Liu, Zheng Wang, Xing-Wang Wang
Summary: The Pd-catalyzed enantioselective linear-allylic alkylation of vinyl benzoxazinanones with 3-substituted oxindoles was achieved using a chiral oxamide-phosphine ligand (COAP-Bn) under mild reaction conditions. The method provided a series of optically active 3,3'-disubstituted oxindole derivatives with a quaternary stereogenic center and a linear aryl amino side chain in good yields (55-98%) and high enantioselectivity (96-99% ee) for 3-(hetero)aryl substituted oxindoles. The COAP ligands demonstrated their capacity to construct diverse chiral 3,3-disubstituted oxindole compounds with various quaternary stereogenic centers.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Jun -Bo Chen, Wen -Kai Liu, Jia-Xin Song, Zheng Wang, Xing-Wang Wang
Summary: A one-pot, five-step domino reaction was developed to synthesize a series of chiral bis-oxalamide palladium(II) complexes with tetraaryl-conjugated substituents in good yields. These complexes exhibited noticeable blue fluorescence under ultraviolet light irradiation.
Article
Chemistry, Organic
Sheng-Suo Zhou, Jun-Hao Shen, Wen-Kai Liu, Xing-Yun Sun, Jia-Yu Song, Zheng Wang, Zheng-Hang Qi, Xing-Wang Wang
Summary: A chiral oxalamide phosphine (COAP)-Pd-catalyzed asymmetric cascade formal [4 + 1] annulation was developed between racemic vinyl benzoxazinones and N-tosylhydrazone sodium salts. The corresponding trans-2,3-disubstituted indoline products with contiguous stereogenic centers were obtained in good yields with high diastereo- and enantioselectivity. The catalytic outcomes and computational DFT study showed that the biphilic transformation proceeded by a dynamic kinetic asymmetric transformation (DYKAT) process. The enantio-determining step is a stereoselective migratory insertion of Pd(ii)-carbene into a pendant chiral p-allylpalladium-COAP complex, followed by reductive elimination to fulfill the annulation.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Jun-Bo Chen, Cheng Peng, Sheng-Suo Zhou, Yong Wang, Zheng Wang, Xing-Wang Wang
Summary: A novel chiral ligand, COAP, was developed for the palladium-catalyzed asymmetric allylic amination, providing enantiomerically enriched compounds in high yields and high enantioselectivities. Mechanistic studies revealed the crucial role of carbonyl coordination in the regio- and enantioselective control of the reaction. The COAP ligand possesses modular structure, fine stereoelectronic tunability, and easy synthesis.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Xiao-Peng Yang, Hao-Peng Lv, Hao-Di Yang, Bai-Lin Wang, Xing-Wang Wang
Summary: Enantioselective copper-catalyzed cascade inter- and intramolecular amidation was achieved between ethynyl benzoxazinanones and alpha-halohydroxamates in the presence of an indapybox ligand. A series of exo-methylene 3-aminoindoline derivatives were obtained in good yields with high enantioselectivities under mild reaction conditions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Nai-Kai Li, Bing-Bing Sun, Jun-Bo Chen, Hao-Di Yang, Bai-Lin Wang, Jie-Qiang Yu, Xing-Wang Wang, Zheng Wang
Summary: This paper demonstrates the asymmetric catalytic synthesis of three series of spirooxindole-pyran derivatives via an inverse-electron-demand oxa-hetero-Diels-Alder reaction. The reactions were carried out with chiral bisoxazoline/copper(ii) complexes as Lewis acid catalysts, resulting in excellent yields with high diastereo- and enantioselectivities under mild reaction conditions.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Bing-Bing Sun, Jun-Bo Chen, Jun-Qi Zhang, Xiao-Peng Yang, Hao-Peng Lv, Zheng Wang, Xing-Wang Wang
ORGANIC CHEMISTRY FRONTIERS
(2020)
Article
Chemistry, Organic
Bing-Bing Sun, Jun-Qi Zhang, Jun-Bo Chen, Wei-Tai Fan, Jie-Qiang Yu, Jia-Ming Hu, Xing-Wang Wang
ORGANIC CHEMISTRY FRONTIERS
(2019)
