Article
Chemistry, Multidisciplinary
Marta Solas, Samuel Suarez-Pantiga, Roberto Sanz
Summary: This study describes the asymmetric synthesis of cyclopentachromenones from gold-catalyzed reaction of readily available skipped alkenynones. The cascade reaction involves an initial anti-Michael hydroarylation and a subsequent Nazarov cyclization. Excellent enantiomeric ratios and chemical yields are achieved under mild reaction conditions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Zhaosheng Liu, Xiaochen Ji, Feng Zhao, Guojun Deng, Huawen Huang
Summary: A novel metal-free photoredox-catalyzed cyclization reaction of N-aryl acrylamide is presented, which produces valuable oxindole derivatives through the mediation of H2O and aldehyde. Sustainable visible light was employed as the energy source, and the organic light-emitting molecule 4CzIPN acted as the efficient photocatalyst. The main features of this reaction are environmentally-friendly conditions and high yields.
Article
Chemistry, Organic
Antonio Arcadi, Giancarlo Fabrizi, Andrea Fochetti, Roberta Franzini, Francesca Ghirga, Antonella Goggiamani, Antonia Iazzetti, Federico Marrone, Andrea Serraiocco
Summary: A regioselective method using a gold (I) catalyst has been developed for the construction of polycyclic chromene cores, with good to excellent yields and a broad range of substrates, providing an efficient tool for synthesizing pyranochromene derivatives. Additionally, the regiochemical control of annulation of unsymmetrically substituted propargylic ethers has been studied, focusing on the electronic/steric effects of gold complexes and the electronic effects of aromatic ring substituents.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Antonio Arcadi, Giancarlo Fabrizi, Andrea Fochetti, Roberta Franzini, Francesca Ghirga, Antonella Goggiamani, Antonia Iazzetti, Federico Marrone, Andrea Serraiocco
Summary: A regioselective gold (I)-catalyzed approach has been developed for constructing polycyclic chromene cores with good to excellent yields under mild conditions, providing an efficient tool for synthesizing pyranochromene derivatives. Investigation into the regiochemical control of the annulation of unsymmetrically substituted propargylic ethers has focused on the electronic/steric effects of the ligands of gold complexes and the electronic effects of groups on the aromatic rings.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Kosho Makino, Shunsuke Sueki, Masahiro Anada
Summary: A Bronsted acid-catalyzed, transition metal-free intramolecular 7-endo hydroarylation reaction of 1,5-diaryl-1-pentynes has been developed. The use of 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as a solvent was found to be critical for this process. Using the present methodology, we have accomplished the synthesis of KGP-18, an analogue of the anticancer natural product combretastatin A4.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Qian Rao, Yin Zhang, Yin-Ping Liu, Bo Jiang, Xiang Wang, Tu Shu-Jiang, Wen-Juan Hao
Summary: A novel gold(I)/Bronsted acid relay catalysis enables the activation of azofuran and induces annulative rearrangement from 3-yne-1,2-diols and aryldiazonium tetrafluoroborates, resulting in the formation of furan-2-yl-substituted pyrrol-2-ones bearing a quaternary carbon center with good yields. Substituting aryldiazonium tetrafluoroborate with azofuran yields structurally identical but substituent-diverse furan-2-yl-containing pyrrol-2-ones with good yields, providing support for the crucial role of azofuran activation and annulative rearrangement by gold/Bronsted acid relay catalysis.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Jian-Bin Lu, Shu-Yuan Liang, Wu-Tao Gui, Zhi-Chao Chen, Wei Du, Ying-Chun Chen
Summary: A relay catalytic protocol utilizing pyrrolidine and palladium catalysis has been developed for the asymmetric synthesis of 1,3-diamine derivatives from 3-substituted 1,3-dienes, sulfuric diamide, and aldehydes. This one-pot, three-component reaction offers the advantages of high atom step economy and operational simplicity, providing an efficient and straightforward access to valuable 1,3-diamines containing quaternary and tertiary stereogenic centers with moderate to good enantioselectivity.
Article
Chemistry, Multidisciplinary
Anthony Aimon, Mark J. Dow, Abigail R. Hanby, Ephraim A. Okolo, Christopher M. Pask, Adam Nelson, Stephen P. Marsden
Summary: The stereocontrolled synthesis of complex spirotricyclic systems containing an embedded syn-1,2-diaminocyclohexane unit is achieved through a dearomatising oxidation of phenols bearing pendant ureas capable of acting as double nucleophiles. The resultant products possess rich functionality suitable for the synthesis of potentially bioactive compounds.
CHEMICAL COMMUNICATIONS
(2023)
Article
Multidisciplinary Sciences
Min Jin, Congyun Tang, Yingying Li, Shuai Yang, Ying-Tao Yang, Lin Peng, Xiao-Nian Li, Wenjing Zhang, Zhili Zuo, Fabien Gagosz, Liang-Liang Wang
Summary: In this study, the authors present a catalytic asymmetric inverse-electron-demand-hetero-Diels-Alder reaction between neutral alkenes and alpha, beta-unsaturated ketones or aldehydes using a chiral phosphoric acid catalyst. This complex transformation allows for the formation of chiral fused heterocycles containing a central tetrahydropyran ring with high regio-, diastereo- and enantioselectivity. The stereocontrol achieved in this process is attributed to a key remote double hydrogen atom bonding interaction between the linear substrate and the catalyst.
NATURE COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Andreas Schneider, Philipp Jegl, Bernhard Hauer
Summary: Cascade reactions provide a cutting-edge strategy for assembling complex structural scaffolds efficiently from naturally available precursors. The research introduced in this report demonstrates a method for controlling cationic cyclization cascades through designed hydrogen bonding, leading to directed cyclizations with high selectivity and yields. This approach offers a more efficient and selective way to access natural compounds such as apocarotenoids, value-added flavors, and fragrances.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Andreas Schneider, Christian Curado, Thomas B. Lystbaek, Silvia Osuna, Bernhard Hauer
Summary: This study uncovers the catalytic potential of squalene-hopene cyclase (SHC) and demonstrates a 397-fold improvement in catalytic performance through tailored mutations. The study also identifies terpene-induced inactivation as a major limitation and proposes a feeding strategy to overcome this limitation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Biochemistry & Molecular Biology
Antonio Arcadi, Andrea Calcaterra, Giancarlo Fabrizi, Andrea Fochetti, Antonella Goggiamani, Antonia Iazzetti, Federico Marrone, Vincenzo Marsicano, Giulia Mazzoccanti, Andrea Serraiocco
Summary: An alternative synthetic route to functionalized 1,2-dihydroquinolines using Au(I) catalysis has been reported. This method is based on the use of N-ethoxycarbonyl protected-N-propargylanilines as building blocks, resulting in good yields. The regiodivergent cyclization at the ortho-/para position is achieved through catalyst fine tuning when N-ethoxycarbonyl-N-propargyl-meta-substituted anilines are present.
Article
Chemistry, Organic
Tao Liu, Tuanli Yao, Ruihua Guo, Xiangyang Qin
Summary: A palladium-catalyzed cascade reaction was developed for the synthesis of tetrahydro-beta-carbolines and other polycyclic indoles from 2-(hydroxyenyl)sulfonanilides by combining Pd(ii)-catalyzed cyclization of alkynes and intramolecular redox-relay Heck arylation of alkenols. This method allows the construction of two rings and installation of a remote carbonyl group in a single operation, offering broad synthetic utility for further elaborations.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
James C. Corcoran, Rui Guo, Yue Xia, Yi-Ming Wang
Summary: In this study, a method for the synthesis of aryl-substituted benzocycloheptenes and -hexenes using vinyl cation mediated Friedel-Crafts cyclization was reported. The hydrotriflate salt of an electron-poor pyridine was used as a unique and efficient proton source in this process. The mild conditions enabled a wide range of alkynes to be used as substrates in this scalable and convenient protocol.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Xin Nie, Zihan Yan, Sergei Ivlev, Eric Meggers
Summary: Enantioselective C(sp(3))-H aminations provide an efficient access to nonracemic chiral amines. This work describes the catalytic asymmetric synthesis of chiral 1,2,5-thiadiazolidine-1,1-dioxides using a recently introduced simple chiral ruthenium bis(oxazoline) complex, achieving high yields and enantioselectivities. Mechanistic experiments confirmed a stepwise mechanism and demonstrated that the cyclic sulfamide products are suitable for the synthesis of chiral vicinal diamines.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
