Article
Chemistry, Organic
Lisheng Wang, Fuxing Yang, Xiaoping Xu, Jun Jiang
Summary: A highly efficient organocatalytic method using bifunctional cinchona alkaloid-based urea has been developed for the enantioselective 1,6-hydrophosphonylation of para-quinone methides derived from isatins. This environmentally friendly protocol provides a straightforward approach to access a variety of chiral 3-phosphoxindoles with phosphorus-substituted quaternary carbon stereocenters, showing high level of chemoselectivity and remote stereocontrol (up to 99% yield, 99 : 1 er).
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Qingfa Tan, Qianping Chen, Zitong Zhu, Xiaohua Liu
Summary: Catalytic enantioselective sulfenylation using chiral guanidine organocatalysts has been developed for the construction of diheteroatom-bearing carbon centres. This method provides a facile route towards the synthesis of various organic compounds with high yields and good to excellent enantioselectivities.
CHEMICAL COMMUNICATIONS
(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, Organic
Eider Dunabeitia, Aitor Landa, Rosa Lopez, Claudio Palomo
Summary: The study demonstrates the capability of bicyclic acylpyrrol lactims to act as pronucleophiles and form carbon-carbon bonds under organocatalytic conditions, leading to the synthesis of chiral pyrrolodiketopiperazines. The use of ureidoaminal-derived Bronsted bases in the Michael addition to nitroolefins allows for the generation of heterocyclic scaffolds with a high degree of skeletal diversity.
Article
Chemistry, Multidisciplinary
Krishna Kumar, Bhuvnesh Singh, Soumyadip Hore, Ravi P. Singh
Summary: A novel catalytic system has been developed for the direct enantioselective vinylogous aldol reaction between 3-alkylidene-2-oxindoles and pyrazole-4,5-diones. The bifunctional quinine-derived benzamide catalyst achieved highly functional rich pyrazolone moieties with excellent E/Z selectivity (>19:1) and high yields, as well as moderate enantioselectivity through H-bonding dual activation mode.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Organic
Abhijit Manna, Harshit Joshi, Vinod K. Singh
Summary: In this study, we report the first ever use of 3-isopropylidene oxindoles as electrophiles in vinylogous Michael initiated ring closure reaction (MIRC). By selectively choosing a more reactive nucleophile, the competing reactivity of isopropylidene oxindoles in the presence of a chiral organocatalyst is controlled. This methodology allows for the synthesis of densely substituted highly enantioenriched spirocyclopropyl oxindoles with excellent yield and stereoselectivities. Additionally, the first enantioselective synthesis of HIV-1 NNRT inhibitor demonstrates the importance of the synthesized spiro-cyclopropyl oxindole core.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Hiroki Mandai, Ryuhei Shiomoto, Kazuki Fujii, Koichi Mitsudo, Seiji Suga
Summary: An efficient acylative kinetic resolution method for 3-hydroxy-3-substituted 2-oxindoles has been developed using a chiral DMAP derivative. The catalyst showed high efficiency with a wide range of substrates and could achieve high resolution within a short reaction time.
Article
Chemistry, Multidisciplinary
Kazutaka Shibatomi
Summary: This paper summarizes our recent efforts in the enantioselective organocatalytic synthesis of chiral halogenated compounds. The discussion includes enantioselective alpha-halogenation of aldehydes, decarboxylative chlorination of beta-keto acids, and enantioselective C-C bond formation at the trifluoromethylated prochiral carbon to yield organohalides with chlorinated, fluorinated, or trifluoromethylated chiral stereogenic centers. Common organocatalysts such as Jorgensen-Hayashi catalyst and cinchona alkaloid-derivatived catalyst were applied, and novel chiral amine catalysts were developed for these reactions. Stereospecific derivatizations of the chiral halogenated compounds via nucleophilic substitution are also discussed, resulting in the synthesis of many novel chiral compounds that have not been reported before, even as racemates.
Article
Chemistry, Medicinal
Andi Yuan, Sarah E. E. Steber, Dea Xhili, Eryn Nelson, Christian Wolf
Summary: Fluorinated oxindoles are commonly used in asymmetric synthesis and are important in biologically relevant compounds. The effects of fluorine incorporation on the configurational stability of chiral organofluorines are not well studied. In this study, semipreparative HPLC enantioseparations were performed on five oxindoles to investigate the base promoted racemization kinetics at room temperature. It was found that fluorine incorporation increases configurational stability, while substitutions on the aromatic ring and lactam moiety also affect racemization rate.
Article
Chemistry, Organic
Min Gao, Yongyi Li, Xuemin Li, Lin Hu
Summary: A new reaction method has been developed for the direct coupling of simple oxindoles with alkyl dihalides, leading to the synthesis of cyclopentane- and cyclohexane-fused spirooxindole scaffolds with high yields and enantioselectivities. The method utilizes general phase-transfer catalysis and shows broad applicability and mild conditions. It also enables gram-scale synthesis of the core of the drug ubrogepant in two steps.
Article
Chemistry, Organic
Jixin Pian, Qingqing Chen, Yujiao Luo, Zhifei Zhao, Jichang Liu, Lin He, Shi-Wu Li
Summary: An enantioselective cyclopropanation reaction of sulfoxonium ylides with beta,gamma-unsaturated ketoesters catalyzed by a chiral rhodium catalyst has been achieved, leading to the synthesis of various optically pure cyclopropanes.
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, Organic
Zheng-Bing Zhang, Qiuzuo He, Ting Wang, Guoqin Wang, Dan Yang, Pan Han, Linhai Jing
Summary: We report the first organocatalytic asymmetric synthesis of densely functionalized spiro-delta-lactam oxindoles with multiple stereogenic centers via a [3 + 3] annulation reaction. This protocol offers a novel, simple, and efficient strategy for synthesizing biologically important spiro-delta-lactam oxindoles using a variety of substrates with excellent diastereoselectivities and enantioselectivities (up to >95:5 dr and 99% ee).
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Ramasamy Jayarajan, Tautvydas Kireilis, Lars Eriksson, Kalman J. Szabo
Summary: In this study, a variety of aliphatic, aromatic, and heterocyclic boronic acids were successfully modified using trifluorodiazoethane and BINOL derivatives, resulting in the synthesis of chiral trifluoromethyl containing boronic acid derivatives. The conversion of the chiral boronic acids to other compounds in situ was also demonstrated.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Organic
Zhanhuan Li, Hongwei Zhou, Jianfeng Xu
Summary: This study describes a rational designed tandem reaction of 2-(1-alkynyl)-2-alken-1-ones with 3-aminobenzofurans enabled by a chiral bifunctional catalyst, producing biologically significant polycyclic 1,4-dihydropyridines in moderate to good yields with good to excellent enantioselectivities. The formal [3 + 3] annulation reaction shows good practicality on a gram scale and the resulting cycloadduct can be further modified.
Article
Chemistry, Multidisciplinary
Long Yin, Junhao Xing, Yuhan Wang, Yue Shen, Tao Lu, Tamio Hayashi, Xiaowei Dou
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
Article
Chemistry, Organic
Xiao Lin, Yuhan Wang, Yan Hu, Wanjiang Zhu, Xiaowei Dou
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Physical
Na Liu, Wanjiang Zhu, Jian Yao, Long Yin, Tao Lu, Xiaowei Dou
Article
Chemistry, Physical
Junhao Xing, Wanjiang Zhu, Bihai Ye, Tao Lu, Tamio Hayashi, Xiaowei Dou
Article
Chemistry, Applied
Huilong Zhu, Long Yin, Zhiqian Chang, Yuhan Wang, Xiaowei Dou
ADVANCED SYNTHESIS & CATALYSIS
(2020)
Article
Chemistry, Applied
Zhiqian Chang, Jian Yao, Xiaowei Dou
ADVANCED SYNTHESIS & CATALYSIS
(2020)
Article
Chemistry, Organic
Yuhan Wang, Zhiqian Chang, Yan Hu, Xiao Lin, Xiaowei Dou
Summary: The diboron-mediated rhodium-catalyzed transfer hydrogenation of functionalized arenes demonstrates good functional group tolerance, operational simplicity, and controllable chemoselectivity. The general applicability of this procedure is shown through the selective hydrogenation of a range of arenes, including functionalized benzenes, biphenyls, and polyaromatics.
Article
Chemistry, Applied
Yan Hu, Chenhong Wang, Huilong Zhu, Junhao Xing, Xiaowei Dou
Summary: A new catalytic method for the synthesis of pyridine-incorporating chiral diarylmethylamines has been developed, providing an effective approach for the preparation of important chiral pharmacophores.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Physical
Bihai Ye, Jian Yao, Changhui Wu, Huilong Zhu, Weijun Yao, Lili Jin, Xiaowei Dou
Summary: In this study, a new rhodium catalyst was developed for the asymmetric conjugate pyridylation reaction with high yields and good enantioselectivities. By optimizing the catalyst and solvent conditions, the challenges of the pyridylation reaction were successfully overcome.
Article
Chemistry, Organic
Huilong Zhu, Junhao Xing, Changhui Wu, Weijun Yao, Xiaowei Dou
Summary: The study achieved the pyridylation of alkynes with pyridylboronic acids under rhodium catalysis, leading to chemodivergent products such as alkenylpyridines and cyclopenta[c]pyridines. Mechanistic investigation revealed that 1,4-rhodium migration to the pyridine ring played a key role in the chemodivergent synthesis.
Article
Chemistry, Physical
Qianqian Zhou, Rong Meng, Junhao Xing, Weijun Yao, Xiaowei Dou
Summary: Transition-metal-catalyzed C-Si bond activation has been used to synthesize diverse organosilicons efficiently. This study presents a rhodium-catalyzed chemodivergent synthesis of organosilicons, enabling the rapid production of allylsilyl ethers, vinylsilanes, oxasilacycles, and beta-silyl ketones from silyl propargyl alcohols and arylboronic acids. The success lies in the controllable on/off switch of C-Si bond activation and selective cleavage of different types of C-Si bonds. This work demonstrates the potential of controllable C-Si activation in transition-metal catalysis.
Article
Chemistry, Organic
Long Yin, Wanjiang Zhu, Yang Xu, Junhao Xing, Xiaowei Dou
Summary: The rhodium-catalyzed ring-opening coupling reaction of cyclic vinyl ethers, including 2,3-dihydrofuran and benzofuran, with organometallic reagents has been reported. The suitable organometallic reagent for 2,3-dihydrofuran and benzofuran was found to be dependent on the substrate, and a plausible mechanism involving different active organorhodium intermediates was proposed for these coupling reactions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Chenhong Wang, Changhui Wu, Yiming Yang, Junhao Xing, Xiaowei Dou
Summary: This study describes an expedient method for the synthesis of indenes through the Rh(i)-catalyzed formal [2 + 2 + 1] annulation between arylboronic acids and alkynes. The proposed reaction process involves intermolecular carborhodation, 1,4-Rh migration, and intramolecular carborhodation, resulting in the formation of three C-C bonds in the indene core.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Zhiqian Chang, Huilong Zhu, Changhui Wu, Junhao Xing, Xiaowei Dou
Summary: The enantioselective synthesis of 2-amino-4H-chromenes via cascade rhodium-catalysed conjugate addition/hetero Thorpe-Ziegler reaction achieved moderate to good yields (up to 98%) and high enantioselectivities (up to 92% ee) using a chiral diene-coordinated rhodium complex as the catalyst. This protocol addresses the methodological deficiency in the asymmetric synthesis of 4-aryl 2-amino-4H-chromenes.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Jian Yao, Na Liu, Long Yin, Junhao Xing, Tao Lu, Xiaowei Dou
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
