Article
Chemistry, Physical
Lei Yu, Wenhai Li, Anyawan Tapdara, Sara Helen Kyne, Mandeep Harode, Rasool Babaahmadi, Alireza Ariafard, Philip Wai Hong Chan
Summary: An efficient chiral gold(I) complex-catalyzed synthetic method for the regio- and enantioselective nitroso-Diels-Alder (NDA) reaction of 1,6-diyne esters with nitrosobenzenes is described. The reaction provides access to a wide range of 3,5,6,8a-tetrahydro-1H-benzo[c][1,2]oxazines as a single regioisomer with high yields and enantiomeric excess values.
Article
Chemistry, Applied
Corentin Antoine Baratay, Wenhai Li, Mitch Mathiew, Lei Yu, Sara Helen Kyne, Weidong Rao, Philip Wai Hong Chan
Summary: A synthetic method for preparing 11H-benzo[a]fluorenes and 13H-indeno[1,2-l]phenanthrenes using gold(I) and Bronsted acid-mediated reactions without excluding moisture or air is described. The reaction mechanism involves gold(I)-catalysed migration and cyclization, followed by rearrangement and deacyloxylative aromatization assisted by Bronsted acid, resulting in the formation of polyaromatic hydrocarbon (PAH) products.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Jingwen Wei, Yangyang Xing, Xiaohan Ye, Bao Nguyen, Lukasz Wojtas, Xin Hong, Xiaodong Shi
Summary: In this study, a new synthetic strategy for enantioselective 1,2-dihydropyridine synthesis was reported. Using the gold-catalyzed intermolecular condensation of amine and diyne-ene, the synthesis was achieved through a formal [3+2+1] fashion with up to 95% yield and up to 99% enantiomeric excess (e.e.).
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Yang-Bo Chen, Li-Gao Liu, Can-Ming Chen, Yi-Xi Liu, Bo Zhou, Xin Lu, Zhou Xu, Long-Wu Ye
Summary: In this study, a copper-catalyzed atroposelective diyne cyclization was disclosed for the synthesis of a range of axially chiral arylpyrrole biaryls with good to excellent yields and enantioselectivities. This method represents the first synthesis of mono-substituted 3-arylpyrrole atropisomers and the first example of atroposelective diyne cyclization and atropisomer construction using vinyl cations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Ashley J. Basson, Mark G. McLaughlin
Summary: The transformation reported is a sustainable, modular, rapid, and high-yielding method for synthesizing densely functionalized 5-aminooxazoles and thiazoles. It is tolerant to a wide range of functional groups and is typically complete in under 30 minutes. The process is environmentally friendly due to the choice of catalyst and solvent, as well as the production of benign alcoholic by-products.
Article
Chemistry, Multidisciplinary
Mohanan Biji, Bernard Prabha, Ravi S. Lankalapalli, Kokkuvayil Vasu Radhakrishnan
Summary: This review highlights the achievements in utilizing zerumbone and its derivatives for developing pharmacologically relevant molecular scaffolds, focusing on transition-metal catalyzed 1,4-conjugate addition reactions, palladium-catalyzed cross-couplings, transition metal-based Lewis acid promoted interrupted Nazarov cyclisation reactions, and photo-induced transformations.
Article
Chemistry, Organic
Dan-Bi Sung, Jong Seok Lee
Summary: This study describes a gold(I)-catalyzed intermolecular formal [2 + 2 + 2] cycloaddition reaction, which selectively synthesizes highly substituted 2H-pyrans using different metal triflate additives. This method provides a new opportunity for the synthesis of other heterocyclic compounds.
Article
Chemistry, Organic
Tian-Shu Zhang, Jing Li, Hua Sun, Shuai Liu, Jing Li, Yan Chen, Wen-Juan Hao, Bo Jiang
Summary: An efficient synthetic approach for the synthesis of cyclopentenones containing a C-C stereocenter using gold(I)-catalyzed Nazarov-type cyclization/1,6-addition of 1,3-enyne esters with p-quinone methides (p-QMs) is described. This tandem transformation showed satisfactory substrate scope and acceptable functional group compatibility, providing a novel protocol for the rapid assembly of cyclopentenones in good to excellent yields under mild reaction conditions.
Article
Chemistry, Organic
Romain Laher, Emilie Gentilini, Christophe Marin, Veronique Michelet
Summary: The study focuses on the synthesis of original structures with bicyclic scaffolds for the fragrance industry and evaluates their potential organoleptic properties. NHC-gold-type catalysts show excellent activities in the synthesis of various bicyclic adducts. The research also compares the similarities and differences between starting ethers and their cycloisomerized bicyclic counterparts.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Multidisciplinary
Ming Dong, Linjun Qi, Jinlong Qian, Shuling Yu, Xiaofeng Tong
Summary: In this study, a Pd(0)-catalyzed hydroacyloxylative cyclization of 1,6-enyne was developed, which proceeds in either a 7-endo-trig or 6-exo-trig fashion when paired with an appropriate dihaloacetic acid reactant. The reaction can produce highly enantiopure seven-membered heterocycles or six-membered rings with moderate enantioselectivity, depending on the substituents on the alkene moiety. Preliminary experimental studies suggest an unusual reaction mechanism involving E-to-Z isomerization of a vinyl-Pd(II) species and alkene trans-oxypalladation, which is governed by the carboxylate selected.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Feng-Lin Hong, Chong-Yang Shi, Pan Hong, Tong-Yi Zhai, Xin-Qi Zhu, Xin Lu, Long-Wu Ye
Summary: In this study, a copper-catalyzed asymmetric cascade cyclization/[1,2]-Stevens-type rearrangement was reported to efficiently assemble a variety of valuable chiral chromeno[3,4-c]pyrroles bearing a quaternary carbon stereocenter with generally moderate to good yields and excellent enantioselectivities (up to 99% ee). Notably, this protocol represents the first example of catalytic asymmetric [1,2]-Stevens-type rearrangement based on alkynes and the first asymmetric formal carbene insertion into the Si-O bond.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Chunxiang Pan, Gaowei Wang, Hengyuan Zhao, Jianxiao Ni, Ruifeng Fan, Yongyun Zhou, Yuanbin Zhu, Shiyuan Wu, Baomin Fan
Summary: An efficient stereoselective cobalt-catalyzed hydrovinylative cyclization of 1,6-enynes with chalcones to obtain functionalized pyrrolidines has been developed. The products were furnished in good yields with up to 93% ee. A plausible mechanism through which the transformation was initiated by cyclization of 1,6-enynes is proposed.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Review
Chemistry, Organic
Milos D. Jovanovic, Milos R. Petkovic, Vladimir M. Savic
Summary: Transition metals, particularly palladium, have played a significant role in the development of novel synthetic processes, with multicomponent cascade reactions allowing for the creation of complex structures from simple starting materials. Recent studies have shown that allenes can exhibit high efficiency and predictable chemoselectivity in Pd-promoted reactions, making them valuable partners in synthetic organic chemistry. The focus on intramolecular processes has led to the discovery of relatively complex polycyclic products with structural features commonly seen in natural products and related compounds.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Applied
Shyam Kumar Banjare, Saista Afreen, Pranav Shridhar Mahulkar, Annapurna Saxena, Ponneri C. Ravikumar
Summary: Here, we report the reactivity of cobalt(III)-catalyst towards hydroarylative functionalization of 1,6-diyne, and unveil the reaction mechanism and the involvement of an ionic pathway.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Physical
John M. Halford-McGuff, Alexandra M. Z. Slawin, Allan J. B. Watson
Summary: This article presents a predictive model for the reactivity and turnover of the Rh-catalyzed [2 + 2 + 2] cycloaddition of diynes and alkynes. Contrary to the proposed electronic model, this model suggests that the reaction is predominantly driven by steric effects, and turnover is proportional to alkyne steric parameters. The model allows for the prediction of catalyst loading, turnover, and reaction yield based on the assessment of the alkyne's steric parameter.
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.