相关参考文献
注意：仅列出部分参考文献，下载原文获取全部文献信息。
Review
Chemistry, Multidisciplinary
Maxim Golfmann et al.
Summary: Bicyclobutanes, highly strained isolable organic compounds, have attracted a lot of attention in organic chemistry due to their low reactivity. In recent years, creative synthetic strategies have been developed to exploit their reactivity, leading to the synthesis of more practical routes. The weak central C-C bond in bicyclobutanes has been utilized in various addition, rearrangement and insertion reactions, offering quick access to complex molecular scaffolds. This review provides an overview of different options for bicyclobutane synthesis, the compounds that can be prepared from bicyclobutanes, and the associated modes of reactivity.
COMMUNICATIONS CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Yujie Liang et al.
Summary: We report a BF3-catalyzed [2 + 2] cycloaddition reaction between aldehydes and bicyclo[1.1.0]butanes (BCBs) to access polysubstituted 2-oxabicyclo[2.1.1]hexanes. A new BCB containing an acyl pyrazole group was discovered, which not only facilitates the reactions but also allows for diverse downstream transformations. Additionally, aryl and vinyl epoxides can be used as substrates that undergo cycloaddition with BCBs after in situ rearrangement to aldehydes. These results will promote the exploration of complex sp(3)-rich bicyclic frameworks and BCB-based cycloaddition chemistry.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Niklas Radhoff et al.
Summary: The design, synthesis, and application of benzene bioisosteres have been a subject of great interest in the past two decades. Recently, bicyclo[2.1.1]hexanes have been established as highly attractive bioisosteres for ortho- and meta-substituted benzenes. In this study, we present a mild, scalable, and transition-metal-free method for constructing highly substituted bicyclo[2.1.1]hexan-2-ones through Lewis acid-catalyzed (3+2)-cycloaddition of bicyclo[1.1.0]-butane ketones with disubstituted ketenes. The reaction exhibits high functional group tolerance, as evidenced by the successful synthesis of various 3-alkyl-3-aryl and 3,3-bisalkyl bicyclo[2.1.1]hexan-2-ones (26 examples, up to 89% yield). Additionally, postfunctionalization of the exocyclic ketone moiety is demonstrated.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Multidisciplinary
Alexander S. Harmata et al.
Summary: The field of strain-driven, radical formal cycloadditions is undergoing a surge in activity, driven by the rise of photoredox catalysis and the demand for sp(3)-rich ring systems. This area has seen significant progress in recent years, with the development of various reactions and the generation of valuable sp(3)-rich ring systems.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Roman Kleinmans et al.
Summary: The ortho-selective intermolecular photocycloaddition of bicyclic aza-arenes is reported, utilizing a strain-release approach. This reaction enables the construction of C-(sp(3))-rich bicyclo-[2.1.1]-hexanes directly connected to N-heteroarenes. Photophysical experiments and DFT calculations reveal the mechanism of this selective intermolecular photocycloaddition.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Multidisciplinary Sciences
Mario P. Wiesenfeldt et al.
Summary: The replacement of benzene rings with sp(3)-hybridized bioisosteres in drug candidates generally improves pharmacokinetic properties while retaining biological activity. Rigid, strained frameworks such as bicyclo[1.1.1]pentane and cubane are particularly well suited as the ring strain imparts high bond strength and thus metabolic stability on their C-H bonds. We report expedient routes to 1,3- and 1,2-disubstituted cubane building blocks using a convenient cyclobutadiene precursor and a photolytic C-H carboxylation reaction, respectively, and develop cross-coupling protocols using copper as a catalyst. Our research enables facile elaboration of all cubane isomers into drug candidates, thus enabling ideal bioisosteric replacement of ortho-, meta-, and para-substituted benzenes.
Article
Chemistry, Multidisciplinary
Soumitra Agasti et al.
Summary: A general synthetic route to substituted bicyclo[2.1.1]hexanes (BCHs) has been developed through intermolecular coupling between olefins and bicyclo[1.1.0]butyl (BCB) ketones. The SmI2-catalysed process can be applied to a wide range of electron-deficient alkenes and substituted BCB ketones, with low loadings of SmI2. The resulting BCH ketones have been shown to be versatile synthetic intermediates and can be used for selective downstream manipulation and the expedient synthesis of a saturated hydrocarbon analogue of the broad-spectrum antimicrobial, phthalylsulfathiazole.
Review
Chemistry, Multidisciplinary
Peter Bellotti et al.
Summary: The concept of strain in organic compounds is essential for understanding the synthesis and properties of organic compounds. Recent advancements in strain-release reactions and photocatalysis have opened up new possibilities for creating unique chemical architectures and expanding the field of strain research.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Multidisciplinary Sciences
Huamin Wang et al.
Summary: In this study, a photoinduced ring enlargement method of thiophenes was developed, which involves the insertion of bicyclo[1.1.0]butanes to form eight-membered bicyclic rings under mild conditions. The synthetic value, broad functional-group compatibility, and excellent chemo- and regioselectivity were demonstrated by scope evaluation and product derivatization. Experimental and computational studies suggested a photoredox-induced radical pathway.
Review
Chemistry, Multidisciplinary
Johannes Grosskopf et al.
Summary: This review provides a comprehensive survey on enantioselective photochemical reactions achieved through triplet sensitization. It is shown that highly selective enantioselective photochemical reactions can be achieved by using appropriate chiral sensitizers or a dual catalytic approach.
Article
Chemistry, Multidisciplinary
Kushal Dhake et al.
Summary: The development of two divergent and complementary Lewis acid catalyzed additions of bicyclobutanes to imines is described. Microscale high-throughput experimentation was integral to the discovery and optimization of both reactions. N-arylimines undergo formal (3+2) cycloaddition with bicyclobutanes to yield azabicyclo[2.1.1]hexanes in a single step; in contrast, N-alkylimines undergo an addition/elimination sequence to generate cyclobutenyl methanamine products with high diastereoselectivity. These new products contain a variety of synthetic handles for further elaboration, including many functional groups relevant to pharmaceutical synthesis. The divergent reactivity observed is attributed to differences in basicity and nucleophilicity of the nitrogen atom in a common carbocation intermediate, leading to either nucleophilic attack (N-aryl) or E1 elimination (N-alkyl).
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Renyu Guo et al.
Summary: Saturated bicycles are increasingly important in the design and development of new pharmaceuticals. This article describes a new strategy for synthesizing bicyclo[2.1.1]hexanes, which have defined exit vectors but are underexplored as building blocks in terms of substitution patterns. The process involves sensitization of a bicyclo[1.1.0]butane followed by cycloaddition with an alkene. The scope and mechanistic details of the method are discussed.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Multidisciplinary Sciences
Roman Kleinmans et al.
Summary: In this study, a new intermolecular [2+2]-photocycloaddition method using bicyclo[1.1.0]butanes as 2 sigma-electron reactants was reported. This reaction was realized by visible-light-mediated triplet energy transfer catalysis. The method allows for a simple, modular, and diastereoselective synthesis of bicyclo[2.1.1]hexanes and extends to a-bonds, providing previously inaccessible structural motifs.
Article
Chemistry, Multidisciplinary
Yongxiang Zheng et al.
Summary: In this study, we have disclosed the first photoinduced [3 sigma + 2 sigma] cycloaddition for the synthesis of trisubstituted bicyclo[3.1.1]heptanes using bicyclo[1.1.0]butanes and cyclopropylamines. This method offers mild and operationally simple conditions, along with unique meta-substituted arene bioisosteres.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Review
Chemistry, Multidisciplinary
Min Zhu et al.
Summary: Exploring the chemical space and developing synthetic methods for molecules with unprecedented structural motifs in organic chemistry are important goals. Dearomatization of arenes, as a unique strategy, provides retrosynthetic disconnections for various molecules with increased saturation and stereoisomerism. However, inherent thermodynamic challenges make further expansion of dearomatization reactions a major problem. Visible-light-induced dearomative cycloaddition reactions have shown potential in synthesizing molecules that are difficult to access by other methods. Regulating the reactivities of transient intermediates in these reactions remains a crucial issue.
ACCOUNTS OF CHEMICAL RESEARCH
(2022)
Article
Chemistry, Multidisciplinary
Roman Bychek et al.
Summary: After more than 20 years of trials, a practical scalable method for synthesizing fluoro-substituted bicyclo[1.1.1]pentanes (F-BCPs) has been developed. The physicochemical properties of F-BCPs were studied, and the core structure was successfully incorporated into the synthesis of the anti-inflammatory drug Flurbiprofen.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Weichen Huang et al.
Summary: Bicyclo[1.1.1]pentane (BCP) motifs have become important in pharmaceutical, agrochemical, and materials chemistry. Most of these structures are obtained through the cleavage of the internal C-C bond in [1.1.1]propellane, using either radicals or metal-based nucleophiles. A multicomponent reaction that allows direct access to complex and diverse disubstituted BCP products is more attractive than current stepwise approaches.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Weizhe Dong et al.
Summary: This study reports a single-step transition-metal-free multi-component approach for synthesizing versatile BCP boronates. Various alkyl-, aryl-, and alkenyl-functionalized BCP boronates were easily prepared by reacting commonly available carboxylic acids and organohalides.
Article
Chemistry, Multidisciplinary
Grace L. Trammel et al.
Summary: Two catalytic systems have been developed for the arylboration of endocyclic enecarbamates, resulting in the synthesis of versatile borylated saturated N-heterocycles with good regio- and diastereoselectivities. The Cu/Pd dual catalytic reaction enables the synthesis of borylated, alpha-arylated azetidines, while the Ni-catalysed arylboration reaction efficiently functionalizes 5-, 6-, and 7-membered enecarbamates. The use of additives in the Cu/Pd system allows for a broader scope of reactions, and the products can be further manipulated to access biologically active compounds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Yujie Liang et al.
Summary: The synthesis of polysubstituted 2-oxabicyclo[2.1.1]hexanes has been achieved in a single step using visible-light-induced triplet energy transfer catalysis. This method offers significant potential in pharmaceutical development, allowing for the rapid construction of complex molecular structures and access to unexplored chemical space.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Multidisciplinary Sciences
Rachel C. Epplin et al.
Summary: The authors report the synthesis and development of ladderanes as replacements for meta-substituted aromatic rings and cyclohexanes. These compounds offer similar metabolic and physicochemical properties, establishing them as interesting motifs for drug discovery.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Pramod Rai et al.
Summary: The article describes a visible-light energy-transfer catalysis method for the intermolecular dearomative [4 + 2] cycloaddition reaction of naphthalene molecules with vinyl benzenes. The method has good functional group tolerance and high yields, and can be used for late-stage modification of pharmaceutical derivatives. The effectiveness of the method is further demonstrated through post-synthetic diversification.
Review
Chemistry, Multidisciplinary
Christopher B. Kelly et al.
Summary: This review discusses the recent developments in the synthesis and functionalization of bicyclo[1.1.0]butane (BCB), as well as the applications of these strained rings in synthesis and drug discovery. BCBs have unique chemistry that has captivated organic chemists for a long time, and recent research has shown that BCBs can be powerful synthetic tools.
Article
Chemistry, Multidisciplinary
Wang Wang et al.
Summary: This article presents a new method for intermolecular dearomative cycloaddition of simple naphthalenes with alkenes, generating bridged bicyclic products with controlled regiochemistry and function. This method is of significant importance in the field of organic chemistry.
Article
Chemistry, Multidisciplinary
Sanghoon Shin et al.
Summary: The formation of an electron donor-acceptor complex allowed for the direct installation of amino and pyridyl groups onto bicyclo[1.1.1]pentane (BCP) frameworks in the absence of an external photocatalyst. This method is robust and metal-free, enabling late-stage modification of structurally complex biorelevant molecules. The strategy also facilitates the incorporation of functional groups with pyridine across the BCP core, significantly expanding the range of potential applications for drug discovery.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Medicinal
Murugaiah A. M. Subbaiah et al.
Summary: The benzene moiety is commonly found in drugs, but its indiscriminate use can lead to poor physicochemical properties. Bioisosteric replacements for benzene rings can improve potency, solubility, and metabolic stability while reducing lipophilicity and other negative effects.
JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Alexander S. Harmata et al.
Summary: In this study, a new method to convert bicyclo[1.1.1]pentan-1-amines to polysubstituted bicyclo[3.1.1]heptan-1-amines through a photochemical reaction of an intermediate imine diradical was reported. Hydrolysis of the imine products provides complex, sp(3)-rich primary amine building blocks. This is the first reported method to convert the bicyclo[1.1.1]pentane skeleton to the bicyclo[3.1.1]heptane skeleton.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Medicinal
Derun Li et al.
Summary: The study successfully synthesized a diverse set of structurally unique bicyclic proline-containing arginase inhibitors with a high degree of three-dimensionality using comprehensive synthetic strategies. Some analogs favored the C gamma-exo conformation of proline, leading to improved arginase potency. These novel synthetic strategies not only enable access to previously unknown stereochemically complex proline derivatives but also lay a foundation for the future synthesis of bicyclic proline analogs.
ACS MEDICINAL CHEMISTRY LETTERS
(2021)
Article
Biochemistry & Molecular Biology
Ivo E. Sampaio-Dias et al.
Summary: Neurodegenerative disorders of the central nervous system represent a global health burden, and research on neuroprotective drugs is considered a health priority. The new analogues designed and synthesized in this study show potential in neuroprotection assays.
ACS CHEMICAL NEUROSCIENCE
(2021)
Article
Chemistry, Multidisciplinary
Helena D. Pickford et al.
Summary: A facile synthesis of 1,3-disubstituted BCPAs using a twofold radical functionalization strategy is reported, allowing for straightforward access to an array of valuable aniline-like isosteres.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Songjie Yu et al.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Organic
Volodymyr V. Semeno et al.
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Multidisciplinary Sciences
Xiaheng Zhang et al.
Article
Chemistry, Multidisciplinary
Aleksandr Denisenko et al.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Review
Chemistry, Multidisciplinary
Quan-Quan Zhou et al.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
Article
Chemistry, Organic
Xiaoshen Ma et al.
Article
Chemistry, Organic
Junichiro Kanazawa et al.
Review
Chemistry, Organic
Pavel K. Mykhailiuk
ORGANIC & BIOMOLECULAR CHEMISTRY
(2019)
Review
Chemistry, Multidisciplinary
Felix Strieth-Kalthoff et al.
CHEMICAL SOCIETY REVIEWS
(2018)
Article
Chemistry, Medicinal
Sebastien L. Degorce et al.
JOURNAL OF MEDICINAL CHEMISTRY
(2018)
Article
Chemistry, Organic
Vadym V. Levterov et al.
JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Multidisciplinary
Junichiro Kanazawa et al.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2017)
Article
Chemistry, Multidisciplinary
Chi Chip Le et al.
ACS CENTRAL SCIENCE
(2017)
Article
Chemistry, Multidisciplinary
Benjamin A. Chalmers et al.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2016)
Article
Chemistry, Multidisciplinary
Josep Cornella et al.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2016)
Review
Chemistry, Organic
Elzbieta Wojaczynska et al.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2015)
Article
Chemistry, Medicinal
Edon Vitaku et al.
JOURNAL OF MEDICINAL CHEMISTRY
(2014)
Article
Biochemistry & Molecular Biology
Frank Lovering
Review
Pharmacology & Pharmacy
Timothy J. Ritchie et al.
DRUG DISCOVERY TODAY
(2009)
Article
Chemistry, Medicinal
Frank Lovering et al.
JOURNAL OF MEDICINAL CHEMISTRY
(2009)
Article
Chemistry, Inorganic & Nuclear
Oleksandr O. Grygorenko et al.
TETRAHEDRON-ASYMMETRY
(2009)
