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Photochemical Catalyst-Free Synthesis of Pyrrolidines via a Hofmann–Loffler–Freytag Reaction [PDF]

Molecules
The Hoffman–Loffler–Freytag (HLF) reaction is one of the first transformations to achieve remote C(sp3)-H functionalization and simultaneously provide useful building blocks from readily available reagents. Herein, we propose a photochemical protocol for
Athina S. J. Shkembi, Luca Pasqualon, Stamatis K. Serviou, Manos V. G. Lantzanakis, Christoforos G. Kokotos   +4 more
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Dialkylaminoalkylation of β-ketosulfones via ring-opening of 3-sulfonylpyrrolidines [PDF]

Beilstein Journal of Organic Chemistry
Herein, a three-step method for the simultaneous dialkylaminoethylation and heteromethylation of active methylene β-ketosulfones, promoted by a leaving benzoyl group, is proposed.
Evgeny M. Buev, Alexander V. Pavlushin, Vladimir S. Moshkin, Vyacheslav Y. Sosnovskikh   +3 more
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Recent Advances in Intramolecular C─N Bond Formation for Pyrrolidine Synthesis [PDF]

ChemistryOpen
Pyrrolidines constitute a privileged class of nitrogen heterocycles that are ubiquitous in pharmaceuticals, bioactive molecules, and functional materials, thereby continuing to stimulate the development of efficient and versatile synthetic strategies ...
Rasma Kroņkalne, Māris Turks
doaj   +2 more sources

Skeletal editing of tetrahydrofurans to pyrrolidines through O-to-N single atom swap [PDF]

Nature Communications
Skeletal editing has emerged as a powerful strategy for organic synthesis, addressing a long-standing synthetic challenge between molecular scaffolds.
Shihan Geng, Tieqiao Wang, Qingxuan Kong, Dunhang Ouyang, Changwei Jiang, Ning Jiao, Song Song   +6 more
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Synthesis of a New Chiral Pyrrolidine [PDF]

Molecules, 2010
The synthesis of a new chiral pyrrolidine has been performed using 2,3-O-isopropylidene-D-erythronolactol as a suitable starting material.
Pilar García, Enrique F. Iglesias, Isidro S. Marcos, Narciso M. Garrido, Rosalina F. Moro, Marta G. Núñez, Mari Fe. Flores, David Díez   +7 more
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One-Pot Route from Halogenated Amides to Piperidines and Pyrrolidines

Molecules, 2022
Piperidine and pyrrolidine derivatives are important nitrogen heterocyclic structures with a wide range of biological activities. However, reported methods for their construction often face problems of requiring the use of expensive metal catalysts ...
Qiao Song, Sheng Wang, Xiangui Lei, Yan Liu, Xin Wen, Zhouyu Wang   +5 more
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Different Behavior of 2-Substituted 3-Nitro-2H-chromenes in the Reaction with Stabilized Azomethine Ylides Generated from α-Iminoesters

Molecules, 2022
The AgOAc-catalysed reaction of 3-nitro-2-phenyl-2H-chromenes with stabilized azomethine ylides generated from the imines based on methyl glycinate and arylaldehydes leads to a mixture of endo and endo’ isomers of the corresponding chromeno[3,4-c ...
Ivan A. Kochnev, Alexey Y. Barkov, Nikita S. Simonov, Maria V. Ulitko, Nikolay S. Zimnitskiy, Vladislav Y. Korotaev, Vyacheslav Y. Sosnovskikh   +6 more
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Regioselective access to polycyclic N-heterocycles via homogeneous copper-catalyzed cascade cyclization of allenynes

Communications Chemistry, 2023
Polycyclic N-heterocycles are important structural motifs commonly found in bioactive compounds, however, their selective construction via the cyclization of allenynes remains challenging yet highly desirable.
Kua-Fei Wei, Qing Liu, Guang Ma, Xiao-Lei Jiang, Xiu-Hong Zhu, Guang-Xin Ru, Wen-Bo Shen   +6 more
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Nitropyridines as 2π-Partners in 1,3-Dipolar Cycloadditions with N-Methyl Azomethine Ylide: An Easy Access to Condensed Pyrrolines

Molecules, 2021
1,3-Dipolar cycloaddition reactions of 2-substituted 5-R-3-nitropyridines and isomeric 3-R-5-nitropyridines with N-methyl azomethine ylide were studied. The effect of the substituent at positions 2 and 5 of the pyridine ring on the possibility of the [3 ...
Maxim A. Bastrakov, Alexey K. Fedorenko, Alexey M. Starosotnikov, Alexander Kh. Shakhnes   +3 more
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Highly stereocontrolled total synthesis of racemic codonopsinol B through isoxazolidine-4,5-diol vinylation

Beilstein Journal of Organic Chemistry, 2021
A new highly diastereoselective synthesis of the polyhydroxylated pyrrolidine alkaloid (±)-codonopsinol B and its N-nor-methyl analogue, starting from achiral materials, is presented.
Lukáš Ďurina, Anna Ďurinová, František Trejtnar, Ľuboš Janotka, Lucia Messingerová, Jana Doháňošová, Ján Moncol, Róbert Fischer   +7 more
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