Article
Chemistry, Organic
Hai-Jun Leng, Qing-Zhu Li, Peng Xiang, Ting Qi, Qing-Song Dai, Zhi-Qiang Jia, Chuan Gou, Xiang Zhang, Jun-Long Li
Summary: A novel oxindole-based azaoxyallyl cation synthons were designed for [3+1] cyclization with sulfur ylides, leading to facile production of 3,3-spiro[beta-lactam]-oxindoles with up to 94% yield and perfect diastereoselectivity.
Article
Chemistry, Multidisciplinary
Song Cheng, Wen Gu, Kun Zhao, Shu Ting Zhang, Lan Yang, Qing Song Liu, Xiao Xiao Li, Zhi Gang Zhao
Summary: A strategy for synthesizing iodo-substituted allylic pyrazoles through NIS-mediated regioselective addition is presented. This reaction is fast, scalable, and tolerant of a wide range of substrates. Additionally, the products can undergo coupling reactions with phenylacetylene under Sonogashira cross-coupling conditions.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Yueyao Chen, Jesse Ling, Angus B. Keto, Yun He, Kam-Hung Low, Elizabeth H. Krenske, Pauline Chiu
Summary: Epoxy and aziridinyl enolsilanes can react as oxyallylic cation equivalents in highly selective and stereoselective intramolecular (3+2) cycloadditions. Computational studies suggest that the stepwise reaction involves the conformational flexibility of the intermediate, which determines the formation of (3+2) cycloadducts. This method can be used for the synthesis of densely functionalized trans-hydrindane scaffolds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Kun Zhao, Qingsong Liu, Song Cheng, Zhigang Zhao, Xiaoxiao Li
Summary: A regioselective hydrothiolation reaction of allenamides with thiophenol was developed via a radical process mediated by PhI(OAc)2, providing an efficient route to vinyl sulfides. The reaction showed good functional group tolerance and high efficiency, resulting in good to excellent yields. Mechanistic investigations revealed that the radical cascade proceeded through an allyl radical intermediate formed by the addition of the PhS radical to the central carbon of allenamides. Furthermore, the reaction was also efficient with selenophenol, yielding the corresponding vinyl selenide in a 99% yield.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Qi Huang, Chuanjiang Xiong, Yungui Peng
Summary: A diastereoselective (3+3) cycloaddition of azomethine imines and in situ-generated azaoxyallyl cations from a-halohydroxamate promoted by a Bronsted base has been developed. A series of pyrazolo [1,2-a][1,2,4]triazin-6-ones were accessed with up to 95% yields and diastereoselectivities greater than 20:1. The asymmetric version of this reaction was explored and moderate enantioselectivity was achieved after screening a series of cinchonine-derived chiral catalysts.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Doris Chen, Elizabeth Jones, Corey W. Williams, Tan-Khang N. Huynh, Tristan C. McPhail, Stefan France
Summary: In this study, a SnCl4-catalyzed intramolecular, interrupted homo-Nazarov cascade biscyclization method was developed to access angular (hetero)aryl-fused polycycles. The cyclopropyl homo-Nazarov cyclization precursors were formed using a scalable and modular synthetic route, enabling the synthesis of various angular polycyclic products. The method was successfully applied in the total synthesis of (+/-)-1-oxoferruginol, an antibacterial aromatic abietane diterpenoid.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Organic
Zhaoqi Wu, Heng Wang, Tianci Chen, Ze-Feng Xu, Chuan-Ying Li
Summary: We present a rhodium-catalyzed intramolecular [4 + 3] cycloaddition reaction of 1-sulfonyl-1,2,3-triazoles, providing an efficient approach for the synthesis of cyclobutane-fused dihydroazepines with moderate to good yields. Furthermore, the reaction enables the construction of three stereocenters, leading to the formation of a single diastereomer in each case. The stereoselectivity control is also discussed.
TETRAHEDRON LETTERS
(2023)
Article
Chemistry, Organic
Lukas Janecky, Athanasios Markos, Blanka Klepetar, Petr Beier
Summary: 4-Aryl-5-allyl-N-fluoroalkyl-1,2,3-triazoles were synthesized through a three-component reaction of fluoroalkyl azides, copper acetylides, and allyl halides. These compounds underwent aluminum halide-mediated transformation to N-(4-halo-2-aryl-cyclopentenyl) imidoyl halides by cyclization of vinyl cation intermediates, followed by halide capture. The cyclic products could be further utilized for the synthesis of N-alkenyl amides, amidines, isoquinolines, and tetrazoles, or for the subsequent modification of the cyclopentene ring.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Fusun Seyma Gungor, B. Sebnem Sesalan, Nurcan Senyurt Tuzun, Yilmaz Ozkilic, Olcay Anac
Summary: The study highlights the importance of diastereoselectivity in carbenoid reactions, with the synthesized metallophthalocyanine catalysts enabling the enrichment of diastereomeric products. By comparing four different metallophthalocyanines, it was found that copper-Pc with neopentyl is the most effective catalyst.
Article
Chemistry, Multidisciplinary
Anastasia Merk, Lukas Buehrmann, Natalie Kordts, Katharina Goertemaker, Marc Schmidtmann, Thomas Mueller
Summary: The stabilizing neighboring effect of halo substituents on silyl cations was tested for a series of peri-halo substituted acenaphthyl-based silyl cations. Different halonium ions show varying levels of Lewis acidity, with fluoronium ion being very strong and iodonium ion being moderate. Additionally, halonium ions can undergo substituent redistribution reactions to form siliconium ions.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Applied
Zhongtao Yang, Xiai Luo, Zhipeng Zhang, Xiaoling Luo, Jia Zheng, Hui Luo, Weiguang Yang
Summary: In this study, a silver-catalyzed [3+2] diastereoselective annulation of p-quinamines and ketenimine zwitterionic salts was successfully carried out, leading to the synthesis of new compounds with specific stereochemical configurations. The relative stereoselectivity of the reaction can be controlled by specific functional groups. This method is significant for expanding the application of ketenimine zwitterionic salts.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Kyu-Hyun Sim, Thameem ul Ansari, Yong-Gyu Park, Yeolib Jeong, Sang-Ha Oh, Hye-Won Min, Da-Yoon Jeon, Hyunwoo Kim, Cheon-Gyu Cho
Summary: This study reports the intramolecular Diels-Alder reactions of 2-pyrones with a chiral branched allylic silyl ether substituent, showing remarkably high pi-facial- and endo-selectivities. The resulting diastereomerically and enantiomerically pure cycloadducts were transformed into the natural products (+)-lycopladine A and (-)-lycoposerramine R.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Inorganic & Nuclear
Vanessa M. Gonzalez, Gyeongjin Park, Mengxi Yang, Francois P. Gabbai
Summary: In this study, a stibonium Lewis acid was synthesized and used to prepare fluorostiborane. The fluorostiborane showed enhanced P=O -> Sb interaction and exhibited significantly higher fluoride anion transport activity in fluoride-containing vesicles compared to traditional antimonium cations.
DALTON TRANSACTIONS
(2021)
Article
Chemistry, Organic
Sota Adachi, Naoya Maeta, Kaii Nakayama, Zimo Wang, Yasuhiro Hashimoto, Yohei Okada
Summary: Both intermolecular and intramolecular electron transfers play important roles in determining the synthetic outcomes of photochemical and electrochemical reactions. In this study, dispersed TiO2 nanoparticles in combination with methoxybenzene were found to be a unique heterogeneous photocatalyst for facilitating the formation of novel cyclobutanes. The results suggest that methoxybenzene is adsorbed onto the TiO2 surface, leading to a pseudo-intramolecular electron transfer with the forming cyclobutane radical cation.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Organic
Miaolin Ke, Bolin Qiao, Yuyan Yu, Xinzhi Li, Xiao Xiao, Shi-Jun Li, Yu Lan, Fener Chen
Summary: We have developed an efficient method for synthesizing multisubstituted tetrahydrofuran scaffolds through Pd-catalyzed reaction, leading to a series of derivatives with high efficiency and excellent stereo selectivity. Density functional theory studies have revealed the role of methanol in the reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
