Article
Chemistry, Multidisciplinary
Nils Ansmann, Thaddaus Thorwart, Lutz Greb
Summary: The Lewis superacid bis(perchlorocatecholato)silane catalyzes C-O bond metathesis of alkyl ethers with high efficiency, enabling chemoselective ring contractions of macrocyclic crown ethers and unprecedented ring-closing metathesis of polyethylene glycols for polymer-selective degradation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Yi Wang, Wei Liao, Yuanyuan Wang, Lei Jiao, Zhi-Xiang Yu
Summary: Through a 15-year investigation, we have delved into the mechanism of the [5 + 2 + 1] cycloaddition, identifying key steps in the catalytic cycle and elucidating the stereochemistry and chemical selectivity of the reaction.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Ridge Michael P. Ylagan, Eric Jaewon Lee, Daniela E. Negru, Paolo Ricci, Bohyun Park, Haram Ryu, Mu-Hyun Baik, P. Andrew Evans
Summary: We report an enantioselective rhodium(I)-catalyzed Pauson-Khand reaction using 1,6-chloroenynes that contain challenging 1,1-disubstituted olefins. Unlike previous studies, this new approach allows for a wider range of substrates, including both carbon and heteroatom tethers with polar and non-polar substituents on the alkene. DFT calculations reveal the critical role of the halide, which pre-polarizes the alkyne and provides the appropriate steric profile for a favorable interaction with the chiral diphosphine ligand.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Organic
Sambasivarao Kotha, Ambareen Fatma
Summary: This article highlights various synthetic methodologies related to tetraquinane frameworks in crinipellin derivatives, including different synthetic strategies and emphasis on the core structure research.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Joan Salto, Maria Biosca, Oscar Pamies, Montserrat Dieguez
Summary: A set of complex tricyclic compounds containing multiple functional groups and stereogenic centers has been synthesized in only two steps with excellent diastereo- and enantioselectivities, using a highly versatile and enantioselective Pd-catalyzed reaction.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Dmitry S. Belov, Gabriela Tejeda, Charlene Tsay, Konstantin V. Bukhryakov
Summary: Vanadium-based catalysts have been demonstrated to catalyze ring-closing olefin metathesis reactions by well-defined V chloride alkylidene phosphine complexes, exhibiting good functional group tolerance. The properties of the imido group and phosphine were found to play a crucial role in the stability of active intermediates.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Annah E. Kalb, Mingxin Liu, Megan Bosso, Christopher Uyeda
Summary: A dinickel catalyst is used to promote the [2 + 2 + 1]-cycloaddition reaction of two aldehyde equivalents and a vinylidene, leading to the synthesis of unsymmetrical alkyl-substituted α-hydroxy ketones. Mechanistic studies show that migratory insertion of the aldehyde and C-O reductive elimination are crucial steps, and under dilute conditions, an enone side product is formed due to competing β-hydride elimination.
Article
Chemistry, Applied
Ravindra S. Phatake, Noy B. Nechmad, Ofer Reany, N. Gabriel Lemcoff
Summary: A selective ring-closing metathesis (RCM) reaction using latent sulfur chelated ruthenium iodide benzylidenes as catalysts, activated by thermal and photochemical stimuli, has been reported. This method enables the formation of large macrocycles with high yields, especially for dienes with one terminal alkene and one internal double bond. For substrates containing two internal double bonds, a sacrificial methylene donor can be used to obtain the desired products.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Biochemistry & Molecular Biology
Anna Brodzka, Dominik Koszelewski, Ryszard Ostaszewski
Summary: The goal of diversity-oriented synthesis is to achieve structural diversity of compounds, but issues with low efficiency and multiple purification steps in kinetic resolution exist. A new concept has been proposed to simultaneously form two skeletally and enantiomerically diverse platform molecules in a one-pot protocol to overcome these limitations.
Article
Chemistry, Applied
Augustin Nouaille, Xavier Pannecoucke, Thomas Poisson, Samuel Couve-Bonnaire
Summary: This study presents an efficient ruthenium-catalyzed CM reaction method, successfully allowing various alkenes to react with methyl 2-fluoroacrylate to obtain trisubstituted fluoroalkenes for the first time. Additionally, an unprecedented TON value for the CM reaction involving fluoroalkenes was achieved, demonstrating good tolerance and effectiveness with a wide range of olefin partners.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Review
Chemistry, Organic
Santhosh Kumar Podiyanachari, Hassan S. Bazzi, Mohammed Al-Hashimi
Summary: Synthesis of cycloolefin-based polymers via metathesis-accompanied cyclopolymerization and tandem ring-opening/ring-closing metathesis (RO/RCM) polymerization leads to highly functional cycloolefin ring-based polymers.
CURRENT ORGANIC CHEMISTRY
(2021)
Article
Polymer Science
Mohammad Yasir, Andreas F. M. Kilbinger
Summary: Norbornene and cyclohexene show different polymerization behaviors using Grubbs' catalysts due to their varying ring strain energy levels; a sequence-selective cascade polymerization of a monomer containing both rings resulted in polymers with moderate molecular weight dispersities and good control over molecular weight.
Article
Chemistry, Organic
Song Liu, Dianmin Zhang, Min Xiao, Chengling Pu, Xiaoqing Zhang, Xiuwen Yang, Tao Zhang, Ruopeng Bai
Summary: C-N bond metathesis is a straightforward and step-economical approach for C-N bond construction. This report presents computational evidence for a new type of reversible reductive elimination/oxidative addition mode in the C-N bond metathesis reaction, which is important for understanding the mechanism of Pd-catalyzed C-N bond formation reactions.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Marina Diaz-Ruiz, Aina Urbina, Nuria Llor, Joan Bosch, Mercedes Amat, Feliu Maseras
Summary: This study reports the synthesis of a marine macrolide and investigates the mechanism of a specific reaction step. The chemoselectivity is found to be controlled by thermodynamics, which is supported by theoretical calculations and experimental studies.
Article
Chemistry, Multidisciplinary
Shu-Xin Zhang, Cong Xu, Niannian Yi, Shan Li, Yan-Mei He, Yu Feng, Qing-Hua Fan
Summary: This study successfully achieved the highly efficient ruthenium-catalyzed enantioselective hydrogenation of 9-phenanthrols by trapping the unstable keto tautomers under mild conditions. The method provides a facile access to chiral 9,10-dihydrophenanthren-9-ols with high yield and enantiomeric excess.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)