Article
Chemistry, Organic
Bohdan A. Chalyk, Andrii Khutorianskyi, Bohdan V. Vashchenko, Kyrylo Danyleiko, Anastasiia Grynyova, Anastasiia O. Osipova, Andriy Kozytskiy, Darya Syniuchenko, Anton Tsymbaliuk, Konstantin S. Gavrilenko, Angelina Biitseva, Dmitriy M. Volochnyuk, Igor Komarov, Oleksandr O. Grygorenko
Summary: This study describes an efficient synthesis method for 3-hydroxypyrrolidin-2-ones bearing alkyl substituents or functional groups at the C-5 position. The reaction sequence involves a 1,3-dipolar cycloaddition reaction followed by catalytic hydrogenolysis, which leads to high selectivity and conversion rates. The method is tolerant to functional groups and can be applied to the synthesis of other compounds.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Jiaqing Xu, Wangyu Shi, Min Liu, Jianning Liao, Wei Wang, Yongjun Wu, Hongchao Guo
Summary: A palladium-catalyzed [4+2] cycloaddition reaction has been developed for the efficient synthesis of tetrahydropyran derivatives with good selectivity.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Hai-Xiang Zeng, Xiao-Wen Zhang, Qi-Yang Li, Wen-Bo Liu
Summary: An enantioselective Ni-catalyzed syn-hydrocyclization reaction was developed for the synthesis of α-hydroxy γ-lactams. By using Ni(OTs)(2)·6H(2)O/(S,S)-Me-Duphos as a precatalyst and (EtO)2MeSiH as a hydride source, a wide range of enantioenriched γ-lactams with fully substituted stereogenic centers were obtained in 32-84% yields with 87.5:12.5-97:3 er. This research provides a regioselective functionalization of alkynes and offers an efficient strategy for accessing functional group-enriched chiral heterocycles.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Lei Li, Li Shi, Kun Wei, Yu-Rong Yang
Summary: The first asymmetric total synthesis of (+)-quinocarcinamide (3), an enantiomer of the natural oxidation product from antitumor antibiotic (-)-quinocarcin (1), is described, involving key steps such as iridium-catalyzed asymmetric allylic amidation of racemic alcohol 9, olefin cross-metathesis, S(N)2' reaction to forge tetrahydroisoquinoline, and stereocontrolled 1,3-dipolar cycloaddition between azomethine ylide and tert-butyl acrylate to construct the diazabicyclo[3.2.1]octane ring.
Article
Chemistry, Organic
Meysam Azizzade, Parviz Rashidi Ranjbar, Akram Sajadi
Summary: A novel regioselective annulation of propargylic alcohols with simple carbazoles has been developed for the synthesis of [3,2,1-jk]carbazole scaffolds. Additionally, in situ synthesis of propargyl alcohols from simple and easily accessible ketones was achieved during the one-pot synthesis of [3,2,1-jk]carbazoles.
Article
Chemistry, Multidisciplinary
Jiajin Xia, Baolong Zhu, Qiuling Wan, Yinghua Yu, Shenlin Huang, Jian Zhang, Xueliang Huang
Summary: Transition metal-catalyzed divergent synthesis through alternation of the catalyst is demonstrated, providing an operationally simple way to access different valuable products from the same reactants. A gold-catalyzed cascade reaction of conjugated diynamides with allylic alcohols is described, giving selectively substituted allenes and furans by varying the catalysts. Mechanistic studies reveal a [3,3]-sigmatropic rearrangement and an intramolecular Himbert arene/allene Diels-Alder cycloaddition as additional reaction sequences to access dearomatized products with bicyclo[2,2,2]octadiene core.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Jin-Fay Tan, Carl Thomas Bormann, Kay Severin, Nicolai Cramer
Summary: The 2-pyrone motif in bioactive natural products can be modified through the properties of 1-alkynyl triazenes with the addition of propiolic acids and subsequent cyclization induced by silver salt. Different triazenyl derivatives of 2-pyrones can be selectively formed depending on reaction temperature and further replaced by various groups, leading to valuable compounds such as 2-fluoro pyrones. The triazenyl group also plays a role in subsequent Diels-Alder cycloadditions and in the formation of rare fused aminopyrazole pyrone heterocycles.
Article
Chemistry, Multidisciplinary
Wu-Bin Zhang, Guang Chen, Shi-Liang Shi
Summary: An innovative method for constructing acyclic quaternary carbon stereocenters from aldehydes, alkynes, and enones through N-heterocyclic carbene (NHC)-Ni catalysis has been successfully developed, with high selectivity and atom economy. This strategy is expected to inspire new and efficient approaches for generating other acyclic quaternary stereocenters.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Biochemistry & Molecular Biology
Carlos Diez-Poza, Asuncion Barbero
Summary: The regioselective ring opening of epoxy alcohols is an effective method for the synthesis of different types of oxacycles. The acid-catalyzed cyclization of epoxysilyl alcohols was studied and different factors influencing the process were investigated, resulting in the selective formation of two types of heterocycles based on the structure of the initial epoxysilyl alcohol.
Article
Polymer Science
Caitlin S. Sample, Elizabeth A. Kellstedt, Marc A. Hillmyer
Summary: In this study, a new hydroxyl-containing chain transfer agent (CTA) was developed, which allowed for the direct synthesis of hydroxy-telechelic polyalkenamers and subsequent hydrogenation using a streamlined catalytic approach. This method offers high atom economy, low waste generation, uses a green solvent, requires minimal catalyst quantity, and does not require additional purification steps.
Article
Chemistry, Organic
Ran Song, Zhendong Lian, Wei Feng, Tianyi Guan, Wen Si, Daoshan Yang, Jian Lv
Summary: A novel palladium-catalyzed decarboxylative O-allylation of phenols was developed. A gamma-methylidene-delta-valerolactone (GMDV) was identified as an efficient and selective allylation reagent, leading to the synthesis of allyl phenyl ethers in high yields under mild conditions.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Physical
Haydar A. Mohammad-Salim, Nivedita Acharjee, Luis R. Domingo, Hassan H. Abdallah
Summary: The study investigated the [3 + 2] cycloaddition reactions of 1-pyrroline-1-oxide with acetylene and a series of symmetrically disubstituted acetylenes. These reactions proceed through a one-step mechanism with different activation enthalpies, and are irreversible, forming new C-C and C-O single bonds.
INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Kun Cui, Yan-Lin Li, Gongqiang Li, Ji-Bao Xia
Summary: A new regio- and stereoselective reductive coupling of alkynes and crotononitrile has been developed using visible light organophotoredox cobalt dual catalysis, resulting in the synthesis of enantioenriched homoallylic nitriles with stereodefined trisubstituted alkene.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Dong-Chao Wang, Peng-Peng Cheng, Ting-Ting Yang, Pan-Pan Wu, Gui-Rong Qu, Hai-Ming Guo
Summary: The palladium-catalyzed enantioselective Heck cyclization/dearomatization cascade via capturing the cyclized Heck pi-allylpalladium intermediate by beta-naphthols provides a new strategy for constructing chiral indole-terpenoid frameworks. This method yields indole-functionalized beta-naphthalenone compounds with all-carbon-substituted quaternary chiral centers in excellent yields (up to 92%) and enantioselectivities (up to 94% ee), with demonstrated utility in gram-scale syntheses and diverse transformations of the dearomatized products.
Article
Chemistry, Organic
Daigo Ninomiya, Shota Nagasawa, Yoshiharu Iwabuchi
Summary: We present an enantiocontrolled approach for the synthesis of highly functionalized clovane-type terpenoids using a versatile intermediate. The starting material (R)-carvone, a commercially available and enantioenriched building block, was employed in an oxygenative strategy, leading to a concise access to a clovane scaffold. Furthermore, the obtained intermediate was successfully utilized in the formal synthesis of rumphellclovane E.
