Review
Chemistry, Organic
Regina Westphal, Eclair Venturini Filho, Fabrizio Medici, Maurizio Benaglia, Sandro J. Greco
Summary: This review summarizes the latest developments in asymmetric domino reactions, with a focus on the preparation of spiro compounds. Discussions on the stereoselectivity of the transformations, reaction mechanisms, rationalization of the stereochemical outcome, and the applications of domino reactions to the synthesis of biologically active molecules and natural products are included.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Multidisciplinary
Ken-Loon Choo, Bijan Mirabi, Karl Z. Demmans, Mark Lautens
Summary: Enantioenriched spiro-oxiranes with three contiguous stereocenters were synthesized using a rhodium-catalyzed cascade reaction, enabling the formation of a spirocyclic framework in a single step. Both sp(2)- and sp-hybridized carbon nucleophiles were found to be efficient initiators, yielding products with different functional groups. Derivatization studies demonstrated the synthetic versatility of the products' epoxide and alkyne moieties. DFT calculations were employed to explain spectroscopic discrepancies between solution- and solid-state structures of the products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Martina Sotolova, Martin Kamlar, Marek Remes, Pierre-Yves Geant, Ivana Cisarova, Martin Sticha, Jan Vesely
Summary: An organocatalytic asymmetric domino Michael/alpha-alkylation reaction has been developed for the synthesis of 1,2,3-trisubstituted cyclopentane carbaldehydes. The reaction, catalyzed by chiral secondary amines, exhibits high diastereo- and enantioselectivities.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Poorna Chandrasekhar Settipalli, Shaik Anwar
Summary: A [2+2+2] annulation reaction between cyclohexanone, beta-nitrostyrene and 2-arylidene-1,3-indanedione has been successfully carried out to obtain multisubstituted spiro trans-decalinol derivatives at room temperature. This reaction process exhibits high chemical yields and excellent diastereoselectivity, resulting in the formation of multiple bonds and stereocenters through the Michael/nitro-Michael/Aldol process.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Applied
Tao Wang, Bo Huang, You-Qing Wang
Summary: Using chiral phosphoric acids as organocatalysts, a formal asymmetric (4+2) cycloaddition of 3-methylene isoindolinone and in situ-generated ortho-quinone methide substrates is achieved. This reaction allows the construction of spiro chroman-isoindolinones containing spiro-N,O-heterocycles with high enantioselectivity, with a broad substrate scope.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Applied
I-Ting Chen, Ren-You Guan, Jeng-Liang Han
Summary: In this study, a catalytic asymmetric vinylogous Mannich/annulation/acylation reaction was developed for the synthesis of chiral spiro-oxindole piperidine derivatives with polyaromatic scaffolds. The reaction provided the desired products in good yields and high enantioselectivity. DFT computational calculations were used to explain the mechanism and origin of the observed enantioselectivity and O-acetylated products.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Review
Chemistry, Organic
Divyang M. Patel, Paras J. Patel, Hitendra M. Patel
Summary: This Review discusses pioneering advances in catalytic stereoselective multicomponent reactions for the preparation of spiro derivatives, highlighting the stereoselective reactions and catalytic mechanisms used in different reactions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Qing-Qing Hang, Shu-Fang Wu, Shuang Yang, Xue Wang, Zhen Zhong, Yu-Chen Zhang, Feng Shi
Summary: The catalytic atroposelective synthesis of axially chiral isochromenone-indoles has been achieved using homophthalic anhydride-based indole derivatives as a new platform molecule for dynamic kinetic resolution. A wide range of axially chiral isochromenone-indoles were synthesized in high yields and excellent enantioselectivities using chiral quaternary ammonium salt as a phase-transfer catalyst in the catalytic asymmetric sulfonylation reaction.
SCIENCE CHINA-CHEMISTRY
(2022)
Article
Chemistry, Applied
Amit Shikari, Koushik Mandal, Deepak Chopra, Subhas Chandra Pan
Summary: A new organocatalytic asymmetric synthesis method has been developed for the synthesis of cyclic acetals with a spirooxindole skeleton. It was found that a bifunctional squaramide catalyst with an adamantyl motif was the most effective in the cascade reaction, providing high diastereo- and enantioselectivities for the desired products.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Review
Chemistry, Organic
Martina Bortolami, Francesca Leonelli, Marta Feroci, Fabrizio Vetica
Summary: Organocatalysis has been shown to be a powerful tool for the asymmetric synthesis of oxindole-based compounds, offering advantages such as step- and atom-economy, environmental friendliness, and non-toxicity.
CURRENT ORGANIC CHEMISTRY
(2021)
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)
Review
Chemistry, Organic
Adrian Lavios, Amparo Sanz-Marco, Carlos Vila, Gonzalo Blay, Jose R. Pedro
Summary: The spirocyclic motif is widely found in natural products, chiral ligands, and pharmacologically active compounds. The formal [3+2] cycloaddition reaction of isothiocyanates or isocyanides with cyclic compounds has been developed for the enantioselective synthesis of aza-spirocyclic compounds, with organocatalysis playing a key role in these reactions. The synthesis of spirooxindoles using this methodology has received particular attention, highlighting the importance of the structure of the dipolarophiles and the isothiocyanate and isocyanide dipoles.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Achille Antenucci, Giovanni Ghigo, Davide Cassetta, Marco Alcibiade, Stefano Dughera
Summary: Chiral phosphoric acids (CPAs) and their salts have been widely used as privileged catalysts in asymmetric transformations. Previous efficient CPAs have relied on C-2 symmetry and axial chirality, with the only exception being TADDOL derivatives. In this study, we have designed and synthesized C-2 symmetric cycloglycerophosphates (cGPAs), which were applied in the addition of trimethylsilyl cyanide (TMSCN) to aldehydes and ketones. The corresponding cyanohydrins were obtained with yields between 77% and 99% and enantiomeric excesses between 84.2% and 99.5%, in 27 examples. A DFT computational model was also used to rationalize the reaction mechanism and stereochemical outcome.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Feng-Tao Sheng, Shuang Yang, Shu-Fang Wu, Yu-Chen Zhang, Feng Shi
Summary: A new strategy for the enantioselective synthesis of axially chiral 3,3'-bisindoles was developed by directly coupling two indole rings using the C3-umpolung reactivity of 2-indolylmethanols. The synthesized compounds can be further modified to create axially chiral 3,3'-bisindole-based organocatalysts for asymmetric catalysis.
CHINESE JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Applied
Byungjun Kim, Sukwoo Lee, Sarah Yunmi Lee
Summary: In this study, a new method was reported to successfully promote the catalytic asymmetric Diels-Alder reactions using a chiral catalyst in conjunction with a chiral isothiourea catalyst or a Bronsted acid, resulting in the synthesis of densely functionalized cyclohexenes with multiple stereocenters.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Applied
Yang Wang, Meng Sun, Lei Yin, Feng Shi
ADVANCED SYNTHESIS & CATALYSIS
(2015)
Article
Chemistry, Organic
Meng Sun, Yang Wang, Lei Yin, Yang-Yan Cao, Feng Shi
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2015)
Article
Chemistry, Organic
Yang Wang, Man-Su Tu, Lei Yin, Meng Sun, Feng Shi
JOURNAL OF ORGANIC CHEMISTRY
(2015)
Article
Chemistry, Applied
Lei Yin, Yang Wang, Meng Sun, Feng Shi
ADVANCED SYNTHESIS & CATALYSIS
(2016)
Article
Chemistry, Organic
Zi-Qi Zhu, Lei Yin, Yang Wang, Yang Shen, Can Li, Guang-Jian Mei, Feng Shi
ORGANIC CHEMISTRY FRONTIERS
(2017)
Article
Chemistry, Organic
Yang Wang, Hang Yuan, Hongfei Lu, Wen-Hua Zheng
Article
Chemistry, Organic
Yang Wang, Cun-Yuan Zhao, Yi-Ping Wang, Wen-Hua Zheng
SYNTHESIS-STUTTGART
(2019)
Article
Chemistry, Organic
Yang Wang, Yuan-Yuan Sun, Yi-Mo Cui, Ying-Xin Yu, Zheng-Guang Wu
Summary: In this study, a high-efficiency synthesis of benzimidazolone derivatives was achieved through the first aryl iodide catalyzed intramolecular C-H amination of phenylurea. The one-step organocatalytic oxidative process was operationally simple and yielded excellent results (up to 97%). The use of fluorinated protic alcohols effectively accelerated the conversion of this transformation, allowing for a cost-effective and readily accessible catalyst.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Yang Wang, Mo Yang, Yuan-Yuan Sun, Zheng-Guang Wu, Hong Dai, Shuhua Li
Summary: In this study, the first intramolecular C-N bond formation of phenylpropanamide derivatives via organocatalytic oxidative reactions was reported, yielding 3,3-disubstituted oxindole derivatives with up to 99% yield. The high efficiency of this reaction is demonstrated by the ability to perform the reaction on a gram scale under transition metal-free mild conditions. Additionally, DFT calculation of the catalytic oxidative transformation pathway was also studied.
Article
Chemistry, Organic
Zhi-Peng Liang, Ying-Xin Yu, Yuan-Yuan Sun, Yang Wang, Zheng-Guang Wu
Summary: An intramolecular oxidative transformation of diphenylpropanamide derivatives catalyzed by aryl iodide is described, which can readily afford the C-N/C-O coupling products in a single step. The diversity of target compound generation in this reaction is determined by the speed of the 1,3-aryl iodide migration process. This straightforward approach can be performed with the use of inexpensive and readily available catalyst, transition-metal-free, mild conditions, and good functional group tolerance.
Article
Biochemistry & Molecular Biology
Zhipeng Liang, Ya-Nan Wu, Yang Wang
Summary: In this study, a novel S(O)(2)-N coupling reaction was developed for the synthesis of sulfonamide compounds under mild conditions, utilizing visible light catalysis and dual copper catalysis. Furthermore, the reaction takes advantage of visible light-induced azides to generate triplet nitrene, allowing for the efficient synthesis of structurally diverse benzenesulfinamides in good yields.
Article
Chemistry, Multidisciplinary
Haiyan Xu, Lanping Hu, Guanghua Zhu, Yueping Zhu, Yang Wang, Zheng-Guang Wu, You Zi, Weichun Huang
Summary: A simple and practical method for synthesizing aromatic halides has been developed using the Lewis base DABCO as a catalyst. This method proceeds conveniently and efficiently at ambient conditions, providing the desired products in good to excellent yields and selectivity.
Article
Chemistry, Inorganic & Nuclear
Zheng-Guang Wu, Bing Yang, Yu-Chen Qiu, Yang Wang, Hong Dai, You-Xuan Zheng, Yi Wang, Lanping Hu, Yi Pan
Summary: Cyclometalated iridium (Ir)(iii) complexes are currently the most promising emitters for OLEDs. Two novel blue Ir(iii) complexes were designed to achieve blue emission and good electron mobility simultaneously, showing improved electroluminescence performances. This provides an effective strategy for the future molecular design of blue Ir(iii) complexes with good electron transport property for OLEDs.
DALTON TRANSACTIONS
(2021)
Review
Chemistry, Organic
Yang Wang, Bing Yang, Zheng-Guang Wu, Zheng-Guang Wu
Summary: Chiral iodoarenes have become increasingly important in enantioselective synthesis and catalysis, with various chiral aryliodine frameworks being explored. By utilizing chiral hypervalent iodine reagents based on the 2-iodoresorcinol core, successful catalytic enantioselective dearomatization of phenol compounds, asymmetric oxidation of alkenes, and enantioselective alpha-functionalization of carbonyl compounds have been achieved, highlighting excellent reactivities in terms of yield and enantioselectivity.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Organic
Xin-Xing Wu, Hao Ye, Hong Dai, Bing Yang, Yang Wang, Shufeng Chen, Lanping Hu
ORGANIC CHEMISTRY FRONTIERS
(2020)
