Article
Chemistry, Applied
Da-Ping Jin, Shi-Qi Cao, Fu Cheng, Ze-Sen Xue, Run-Ze Li, Yan-Lin Pu, Dao-Yong Zhu, Wen Bao, Xue-Tao Xu, Shao-Hua Wang
Summary: An Au(I)-catalyzed cascade reaction involving cyclization and semipinacol rearrangement of 1,6-enynes has been developed for the synthesis of spiro[4.5]decanes and 7-azaspiro[4.5]decanes. The use of JohnPhosAuCl/NaBARF catalyst led to the formation of functionalizable spirocyclic products with high diastereoselectivity ranging from 6.7:1 to > 20:1 dr. A plausible reaction mechanism has been proposed based on previous literature and experimental findings.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Liselle Atkin, Hannah J. Ross, Daniel L. Priebbenow
Summary: This study investigates the reactivity of acylsilanes and reveals the participation of light-induced siloxy carbenes in intramolecular reactions. Structural misassignments in previous studies are corrected.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Organic
Shimin Jiang, Haojie Ma, Ruchun Yang, Xian-Rong Song, Qiang Xiao
Summary: Carbo- and heterocycles play crucial roles in drugs, natural products, fine chemicals, and biologically and pharmaceutically active compounds. The development of general, practical, and efficient synthetic approaches to prepare these compounds has attracted significant attention from organic chemists. Cascade cyclization of enynols and diynols has become a powerful tool for constructing various frameworks.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Chenlong Zhu, Thomas R. Hoye
Summary: In this report, a new variant of the HDDA process is revealed, which reduces the activation barrier for the reaction by introducing a central quaternized nitrogen atom. Furthermore, the cyclization of substrates can be achieved spontaneously at room temperature.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Debayan Roy, Beeraiah Baire
Summary: A new domino cyclative approach for the synthesis of polycyclic gamma-butenolides from beta-aryl-Z-enoate propargylic alcohols has been developed, showing potential atropisomerism and representing a novel example in organic chemistry. The synthesis process involves constructing both rings synchronously while creating a potential stereogenic rotational axis.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Physical
Rohit Kumar Maurya, Swadhapriya Bhukta, Keshav Kishor, Rana Chatterjee, Amarender Goud Burra, Mahender Khatravath, Rambabu Dandela
Summary: Boron-containing organometallic compounds have always intrigued organic chemists due to their wide application in carbon-carbon bond formation reactions. This review focuses on the arylative cyclization reactions using boronic acids as substrates under different transition metals, for the synthesis of densely functionalized heterocycles and bioactive scaffolds. The study highlights the growing interest in the field and provides an overview of recent developments.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Multidisciplinary
Jun-Jie Yin, Yun-Peng Wang, Jun Xue, Feng-Fan Zhou, Xing-Qian Shan, Rong Zhu, Kun Fang, Lei Shi, Shu-Yu Zhang, Si-Hua Hou, Wujiong Xia, Yong-Qiang Tu
Summary: The first total syntheses of polycyclic diterpenes phomopsene (1), methyl phomopsenonate (2), and iso-phomopsene (3) have been achieved through an unusual cascade reorganization of C-C single bonds. This approach involves a synergistic Nazarov cyclization/double ring expansion for rapid and stereospecific construction of the tetraquinane scaffold, as well as a one-pot strategic ring expansion through Beckmann fragmentation/recombination to efficiently assemble the tetracyclic skeleton. The correct structure of iso-phomopsene was determined to be the C7 epimer of the originally assigned structure, and the absolute configurations of the target molecules were confirmed through enantioselective synthesis.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Aleksa Milosavljevic, Connor Holt, Alison J. Frontier
Summary: Herein, a one-pot nitrogen-interrupted halo-Prins/halo-Nazarov coupling cascade is reported, which enables the synthesis of functionalized cyclopenta[b]indolines with up to four contiguous stereocenters by joining an enyne and a carbonyl partner. A general method for alkynyl halo-Prins reaction of ketones is provided for the first time, allowing the formation of quaternary stereocenters. The outcomes of secondary alcohol enyne couplings and the impact of aniline enyne substituents on the reaction are also described.
Review
Chemistry, Multidisciplinary
Liang Zou, Yuan Gao, Qiaoman Zhang, Xiang-Yang Ye, Tian Xie, Li-Wei Wang, Yang Ye
Summary: The domino cyclization/coupling strategy is an effective method to produce cyclized and multi-functionalized compounds from olefins, attracting significant attention for its enantiocontrol potential. Recent studies have focused on achieving difunctionalization of substituted olefins through an asymmetric domino intramolecular cyclization/cascade reaction, which is useful for synthesizing complex natural products and drugs. This review provides a classification of reaction types and summarizes the recent advances in this field, serving as a knowledge resource and accelerating research progress.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Organic
Peter Langer
Summary: The domino reactions of heterocyclic enamines with chromone derivatives lead to the synthesis of a variety of annulated heterocyclic ring systems, with the reaction pathway depending on the substituent at position 3 of the chromone. Functional groups at the carbonyl group of the chromone at position 3 allow for further synthetic transformations, including additional ring closures.
Article
Chemistry, Multidisciplinary
Jonay Gonzalez, Pablo Sevilla, Guillem Gabarro-Riera, Jesus Jover, Jorge Echeverria, Sara Fuertes, Ana Arauzo, Elena Bartolome, E. Carolina Sanudo
Summary: This study reported the microwave assisted synthesis of a bidimensional (2D) metal–organic framework (MOF). The material exhibits single-ion magnet behavior and can be exfoliated into stable nanosheets by sonication.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Organic
Xinyue Zhou, Zongxian Liang, Xiao-Na Wang
Summary: Ynamides, as a subgroup of heteroatom-substituted alkynes, have unique structural characteristics that balance reactivity and stability. They have become versatile organic synthons applicable to a diverse array of transformations, especially in the field of ring-forming reactions for natural product syntheses. Their involvement in various ring-forming reactions has led to a dramatic increase in publications over the past few years.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Jiwon Jang, Hanbyul Kim, Seunghoon Shin
Summary: This study reports a revised mechanism for the gold-catalyzed enantioselective thioallylation of propiolates, which delivers highly enantio-enriched alpha-allyl-beta-thioacrylates. The research reveals that the competitive binding of thioethers as nucleophiles to the catalytic site inhibits its activity. The revised mechanism suggests that the conjugate addition of thioethers is the slowest step, followed by a rapid rearrangement, indicating the efficacy of the sulfonium-based approach in accelerating Claisen rearrangement.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Meng-Ling Lin, Ting Zheng, Hao Liu, Ying-Xu Wang, Lin Dong
Summary: Despite the existence of many studies on benzofuran-derived azadienes, there have been few reports on multi-component studies on this heterocyclic skeleton. This paper presents the first cascade three-component acyloxylation of diazo compounds with acids and azadienes under mild conditions. The reaction is applicable to various (A/A) diazo compounds, resulting in the generation of diverse complex benzofuran derivatives.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Jing Gong, Qian Wang, Jieping Zhu
Summary: Alkene difunctionalization featuring an intramolecular carbometallation step has been developed to achieve the transformation of converting alkenes into valuable products. This study reports a novel method for 6-endo-trig carbofluorination by combining the conventional 5-exo-trig carbopalladation with a chemoselective 1,2-aryl/Pd dyotropic rearrangement. The resulting reaction products are chromanes with a tertiary alkyl fluoride function. The reaction mechanism is elucidated through X-ray crystallographic analysis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
