Article
Chemistry, Multidisciplinary
Shrikant D. Tambe, Cheol Hyeon Ka, Ho Seong Hwang, Jaehan Bae, Naeem Iqbal, Eun Jin Cho
Summary: The synthesis of highly functionalized chiral 3-pyrrolines is important for the production of natural and synthetic bioactive molecules. Previous methods using allenoates could not synthesize 3,4-disubstituted 3-pyrrolines. This study presents a novel approach to produce 2,3,4-trisubstituted chiral 3-pyrrolines through a highly stereoselective process using a Ni-II/Fc-i-PrPHOX catalytic system.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Ziyi Zhang, Jin Wang, Shenghai Guo, Jing Fan, Xuesen Fan
Summary: We report an efficient strategy for preparing 5H-phthalazino[1,2-b]quinazolin-8(6H)-one derivatives through a t-BuOK-catalyzed intramolecular hydroamination reaction of functionalized quinazolinones. The reaction proceeds under mild conditions and yields the desired products in good to high yields via exclusive 6-exo-dig cyclization. This protocol offers readily available starting materials, broad substrate scope, and high regio- and stereoselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Xiao-Qian Zhang, Tianyi Xu, Congdi Zhang, Chao Wang, Youliang Wang
Summary: This research reports a new gold-catalyzed formal cycloaddition reaction that utilizes readily available alkynes and amino but/pent-2-enoate derivatives as reactants to synthesize highly functionalized 2,3-dihydropyrroles and 1,2,3,4-tetrahydropyridines. The reaction shows high efficiency and a broad substrate scope, and can be easily performed at the millimole scale. The resulting products can be further transformed into other valuable N-heterocycles.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Applied
Srinivasarao Yaragorla, Dandugula Sneha Latha, Pallava Rajesh
Summary: The study introduced a simple and efficient One-Pot three-component reaction using tert-propargyl alcohols, primary amines, and acyl ketones to synthesize fully substituted pyrroles and pyridine derivatives. A green calcium catalyst was employed to facilitate the formation of β-amino allene intermediate, leading to fully substituted five and six-membered azacyclic compounds through subsequent hydroamination and deacylation reactions.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Physical
Xian Xu, Xizhou Zheng, Xin Xu
Summary: A redox-neutral C-H/N-H annulation of anilines with allenes and dienes was achieved using a scandium catalyst with a simple beta-diketiminato ligand. The reaction selectively produced a family of tetrahydroquinolines in high isolated yields, with both allene and diene coupling partners serving as three-carbon building blocks. Mechanistic investigations suggested a reaction pathway involving N-H allylation, Hofmann-Martius rearrangement, and hydroamination cyclization.
Article
Chemistry, Organic
Pei-Pei Xu, Jun-Yi Liao, Jia-Jie Zhang, Wei-Min Shi, Cui Liang, Gui-Fa Su, Dong-Liang Mo
Summary: Various N-vinylindoles and N-vinylpyrroles were synthesized in moderate to good yields through nickel(II)-catalyzed [3 + 2] cycloaddition. A rational mechanism for the formation of N-vinylindoles was proposed based on labeled experiments and key intermediates detected by mass spectrometry. The method highlights nickel(II)-controlled cyclization, atom-economical reaction, broad substrate scope, good functional group tolerance, and high Z-stereoselectivity.
Article
Chemistry, Organic
Arne G. A. Geissler, Jasmin R. Riesterer, Bernhard Breit
Summary: The intramolecular addition of tosylureas to allenes is highly diastereoselective with palladium or rhodium catalysis, yielding 1,3-cyclic ureas. Palladium catalysis allows access to thermodynamic anti-tetrahydropyrimidinones, while rhodium catalysis enables synthesis of kinetic syn-tetrahydropyrimidinones, both with excellent yields and diastereoselectivities. The obtained tetrahydropyrimidinones are easily deprotected and modified, demonstrating their synthetic value.
Article
Chemistry, Organic
Lucas Pages, Sebastien Lemouzy, Marc Taillefer, Florian Monnier
Summary: The study describes a Brønsted acid-mediated addition reaction of (hetero)aryl and (cyclo)alkyl sodium sulfinates to N-allenyl derivatives, which proceeds smoothly in water. This reaction provides a practical and efficient protocol for the regio- and stereoselective synthesis of allylic sulfones in an atom- and step-economic fashion.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Zhiyao Zheng, Luca Deiana, Daniels Posevins, Abdolrahim A. Rafi, Kaiheng Zhang, Magnus J. Johansson, Cheuk-Wai Tai, Armando Cordova, Jan-E Backvall
Summary: In this study, an efficient nanocopper-catalyzed Alder-ene reaction of allenynamides is described. Copper nanoparticles were immobilized on amino-functionalized micro-crystalline cellulose. The reaction exhibited solvent-controlled chemoselectivity, leading to the synthesis of pyrrolines and pyrroles. The heterogeneous copper catalyst showed high efficiency and recyclability in the Alder-ene reaction, making it a highly attractive catalytic system from an economic and environmental perspective.
Article
Chemistry, Inorganic & Nuclear
Philipp C. Stegner, Jonathan Eyselein, Gerd M. Ballmann, Jens Langer, Jochen Schmidt, Sjoerd Harder
Summary: The chiral building block (R)-(+)-2,2 '-diamino-1,1 '-binaphthyl, (R)-BINAM, was converted to N-substituted proligands and alkaline earth metal catalysts. Quadrant models analysis showed that ligands with specific substituents provided the best steric discrimination in enantioselective intramolecular alkene hydroamination reactions.
DALTON TRANSACTIONS
(2021)
Article
Chemistry, Multidisciplinary
Tingting Feng, Canxiang Liu, Zhen Wu, Xinxin Wu, Chen Zhu
Summary: This report describes a manganese-catalyzed radical [3 + 2] cyclization reaction of cyclopropanols and oxime ethers, providing an efficient approach for the synthesis of structurally diverse 1-pyrrolines.
Review
Chemistry, Multidisciplinary
Senjie Ma, John F. Hartwig
Summary: Catalytic intermolecular hydroamination of alkenes is a valuable method for the synthesis of amines with important applications in various fields. However, achieving high yield and selectivity is challenging due to the lack of thermodynamic driving force and the occurrence of side reactions. Late transition-metal complexes have shown advantages in catalyzing hydroaminations. This Account describes the progress in catalytic hydroamination reactions catalyzed by late transition-metal complexes, including additions to activated and unactivated alkenes, and the development of enantioselective hydroaminations.
ACCOUNTS OF CHEMICAL RESEARCH
(2023)
Article
Chemistry, Organic
Ivan A. Bidusenko, Elena Yu Schmidt, Igor A. Ushakov, Alexander V. Vashchenko, Boris A. Trofimov
Summary: N-Benzyl ketimines undergo [3 + 2] cycloaddition with arylacetylenes in KOBut/DMSO solution to yield 2,3,5-triarylpyrrolines, which can be oxidized in situ to 2,3,5-triaryl-2H-pyrroles in 53-71% yields. Intermediate 1-pyrrolines can be isolated in yields ranging from 31-91% and separately oxidized to the corresponding 2H-pyrroles.
Article
Chemistry, Organic
Jun-Sheng Wei, Song Yang, Yin Wei, Sima Shamsaddinimotlagh, Hossein Tavakol, Min Shi
Summary: A gold(i)-catalyzed intramolecular cyclization reaction was developed to synthesize functionalized morpholines, piperazines, and oxazepanes. The reaction proceeds via a carbene or non-carbene process and exhibits a broad substrate scope, good functional group tolerance, and mild reaction conditions. The reaction pathway can be modulated by the steric bulkiness or chain length of the substrate.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Lulu Shen, Yin Zheng, Zitong Lin, Tianzhu Qin, Zhongxing Huang, Weiwei Zi
Summary: In this study, a binuclear copper-catalyzed method was developed to generate 2-aminoallyl cations from ethynyl methylene cyclic carbamates, which were then used for the enantioselective (3+2) cycloaddition reaction with indoles to construct chiral pyrroloindolines. This transformation exhibits a novel C1,N-dipolar reactivity for 2-aminoallyl cations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
