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Your search keyword '"Van der Eycken, Erik"' showing total 18 results
Start Over Author "Van der Eycken, Erik" Publication Type Electronic Resources
18 results on '"Van der Eycken, Erik"'

1. A Gold(I)-Catalyzed Hydroamination/Cycloisomerization Cascade: Concise Synthesis of (±)-seco-Antofine and (±)-Septicine

Author

UCL - SST/IMCN - Institute of Condensed Matter and Nanosciences, Tian, Guilong, Song, Liangliang, Li, Zhenghua, Robeyns, Koen, Van Meervelt, Luc, Van der Eycken, Erik V., UCL - SST/IMCN - Institute of Condensed Matter and Nanosciences, Tian, Guilong, Song, Liangliang, Li, Zhenghua, Robeyns, Koen, Van Meervelt, Luc, and Van der Eycken, Erik V.

Abstract

A concise and flexible procedure for the synthesis of highly functionalized N-heterocyclic 1,6-annulated 2-pyridones and 2,3-annulated 4-pyrimidinones has been elaborated through a gold-catalyzed tandem hydroamination/cycloisomerization cascade. This novel and highly efficient method allows the rapid construction of these diverse N-heterocyclic scaffolds starting from readily available building blocks, and shows a wide scope and good functional group tolerance. The total synthesis of (±)-seco-antofine and (±)-septicine were realized employing this strategy.

Published
2020

2. Intramolecular cascade annulation triggered by C H activation via rhodium hydride intermediate

Author

UCL - SST/IMCN/MOST - Molecules, Solids and Reactivity, Song, Liangliang, Zhang, Xiaoyong, Tian, Guilong, Robeyns, Koen, Van Meervelt, Luc, Harvey, Jeremy N., Van der Eycken, Erik V., UCL - SST/IMCN/MOST - Molecules, Solids and Reactivity, Song, Liangliang, Zhang, Xiaoyong, Tian, Guilong, Robeyns, Koen, Van Meervelt, Luc, Harvey, Jeremy N., and Van der Eycken, Erik V.

Abstract

A novel intramolecular cascade annulation of O-substituted N-hydroxybenzamides for the synthesis of indolizinones triggered by rhodium(III)-catalyzed sequential C(sp2)-H activation and C(sp3)-H amination is developed. This method features air as the oxidant, a broad substrate scope and excellent functional-group tolerance, including various heterocyclic substrates. The applicaton of indolizinone products with aminal functionality is demonstrated by further derivatization. Mechanistic studies and DFT calculations indicate that two pathways are involved in the formation of indolizinones via rhodium hydride intermediate.

Published
2019

3. Synthesis of functionalized furopyrazines as restricted dipeptidomimetics

Author

Claerhout, Stijn, Sharma, Sweta, Sköld, Christian, Cavaluzzo, Claudia, Sandström, Anja, Larhed, Mats, Thirumal, Meganathan, Parmar, Virinder S., Van der Eycken, Erik V., Claerhout, Stijn, Sharma, Sweta, Sköld, Christian, Cavaluzzo, Claudia, Sandström, Anja, Larhed, Mats, Thirumal, Meganathan, Parmar, Virinder S., and Van der Eycken, Erik V.

Abstract

Herein, an efficient synthetic approach to a furopyrazine scaffold with four points of diversity, starting from 2(1H)-pyrazinones, with dipeptomimetic properties, is presented. R-groups corresponding to amino acid side chains were introduced during the 2(1H)-pyrazinone and subsequent furopyrazine formation. The furopyrazine scaffold was further functionalized with an amino- and a carboxy-terminus resulting in a conformationally restricted dipeptidomimetic scaffold. The carboxy-terminus was introduced via a chemoselective vinylation of the 7-position followed by oxidative cleavage, while the amino-terminus was obtained via Buchwald-Hartwig amidation of the 2-position of the scaffold. The versatility of the synthetic method was demonstrated by the synthesis of a small library of diversely substituted furopyrazines having various amino acid side chains on the four points of diversity. Evaluation with an X-ray structure of the scaffold and computational analysis supports the exploitation of the furopyrazine scaffold as a restricted dipeptide mimic, which can mimic the two central residues of a beta-turn.

Published
2012
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4. Synthesis and biological activity evaluation of N-protected isatin derivatives as inhibitors of ICAM-1 expression on human endothelial cells

Author

Malhotra, Shashwat, Balwani, Sakshi, Dhawan, Ashish, Singh, Brajendra K., Kumar, Sarvesh, Thimmulappa, Rajesh, Biswal, Shyam, Olsen, Carl Erik, Van der Eycken, Erik, Prasad, Ashok K., Ghosh, Balaram, Parmar, Virinder S., Malhotra, Shashwat, Balwani, Sakshi, Dhawan, Ashish, Singh, Brajendra K., Kumar, Sarvesh, Thimmulappa, Rajesh, Biswal, Shyam, Olsen, Carl Erik, Van der Eycken, Erik, Prasad, Ashok K., Ghosh, Balaram, and Parmar, Virinder S.

Published
2011

5. Novel natural product-based cinnamates and their thio and thiono analogs as potent inhibitors of cell adhesion molecules on human endothelial cells

Author

Kumar, Sarvesh, Singh, Brajendra K., Arya, Pragya, Malhotra, Shashwat, Thimmulappa, Rajesh, Prasad, Ashok K., Van der Eycken, Erik, Olsen, Carl Erik, DePass, Anthony L., Biswal, Shyam, Parmar, Virinder S., Ghosh, Balaram, Kumar, Sarvesh, Singh, Brajendra K., Arya, Pragya, Malhotra, Shashwat, Thimmulappa, Rajesh, Prasad, Ashok K., Van der Eycken, Erik, Olsen, Carl Erik, DePass, Anthony L., Biswal, Shyam, Parmar, Virinder S., and Ghosh, Balaram

Published
2011

6. Novel natural product-based cinnamates and their thio and thiono analogs as potent inhibitors of cell adhesion molecules on human endothelial cells

Author

Kumar, Sarvesh, Singh, Brajendra K., Arya, Pragya, Malhotra, Shashwat, Thimmulappa, Rajesh, Prasad, Ashok K., Van der Eycken, Erik, Olsen, Carl Erik, DePass, Anthony L., Biswal, Shyam, Parmar, Virinder S., Ghosh, Balaram, Kumar, Sarvesh, Singh, Brajendra K., Arya, Pragya, Malhotra, Shashwat, Thimmulappa, Rajesh, Prasad, Ashok K., Van der Eycken, Erik, Olsen, Carl Erik, DePass, Anthony L., Biswal, Shyam, Parmar, Virinder S., and Ghosh, Balaram

Published
2011

7. Synthesis and biological activity evaluation of N-protected isatin derivatives as inhibitors of ICAM-1 expression on human endothelial cells

Author

Malhotra, Shashwat, Balwani, Sakshi, Dhawan, Ashish, Singh, Brajendra K., Kumar, Sarvesh, Thimmulappa, Rajesh, Biswal, Shyam, Olsen, Carl Erik, Van der Eycken, Erik, Prasad, Ashok K., Ghosh, Balaram, Parmar, Virinder S., Malhotra, Shashwat, Balwani, Sakshi, Dhawan, Ashish, Singh, Brajendra K., Kumar, Sarvesh, Thimmulappa, Rajesh, Biswal, Shyam, Olsen, Carl Erik, Van der Eycken, Erik, Prasad, Ashok K., Ghosh, Balaram, and Parmar, Virinder S.

Published
2011

8. Synthesis and biological activity evaluation of N-protected isatin derivatives as inhibitors of ICAM-1 expression on human endothelial cells

Author

Malhotra, Shashwat, Balwani, Sakshi, Dhawan, Ashish, Singh, Brajendra K., Kumar, Sarvesh, Thimmulappa, Rajesh, Biswal, Shyam, Olsen, Carl Erik, Van der Eycken, Erik, Prasad, Ashok K., Ghosh, Balaram, Parmar, Virinder S., Malhotra, Shashwat, Balwani, Sakshi, Dhawan, Ashish, Singh, Brajendra K., Kumar, Sarvesh, Thimmulappa, Rajesh, Biswal, Shyam, Olsen, Carl Erik, Van der Eycken, Erik, Prasad, Ashok K., Ghosh, Balaram, and Parmar, Virinder S.

Published
2011

9. Novel natural product-based cinnamates and their thio and thiono analogs as potent inhibitors of cell adhesion molecules on human endothelial cells

Author

Kumar, Sarvesh, Singh, Brajendra K., Arya, Pragya, Malhotra, Shashwat, Thimmulappa, Rajesh, Prasad, Ashok K., Van der Eycken, Erik, Olsen, Carl Erik, DePass, Anthony L., Biswal, Shyam, Parmar, Virinder S., Ghosh, Balaram, Kumar, Sarvesh, Singh, Brajendra K., Arya, Pragya, Malhotra, Shashwat, Thimmulappa, Rajesh, Prasad, Ashok K., Van der Eycken, Erik, Olsen, Carl Erik, DePass, Anthony L., Biswal, Shyam, Parmar, Virinder S., and Ghosh, Balaram

Published
2011

10. Enantioselective biocatalytic reactions on (±)-aryl alkyl ketones with native and modified porcine pancreatic lipase

Author

Husain, Mofazzal, Kumar, Vineet, Kumar, Rajesh, Shakil, Najam A., Sharma, Sunil K., Prasad, Ashok K., Olsen, Carl Erik, Gupta, Rajendra K., Malhotra, Sanjay V., Van Der Eycken, Erik, Depass, Anthony L., Levon, Kalle, Parmar, Virinder S., Husain, Mofazzal, Kumar, Vineet, Kumar, Rajesh, Shakil, Najam A., Sharma, Sunil K., Prasad, Ashok K., Olsen, Carl Erik, Gupta, Rajendra K., Malhotra, Sanjay V., Van Der Eycken, Erik, Depass, Anthony L., Levon, Kalle, and Parmar, Virinder S.

Published
2010

11. Enantioselective biocatalytic reactions on (±)-aryl alkyl ketones with native and modified porcine pancreatic lipase

Author

Husain, Mofazzal, Kumar, Vineet, Kumar, Rajesh, Shakil, Najam A., Sharma, Sunil K., Prasad, Ashok K., Olsen, Carl Erik, Gupta, Rajendra K., Malhotra, Sanjay V., Van Der Eycken, Erik, Depass, Anthony L., Levon, Kalle, Parmar, Virinder S., Husain, Mofazzal, Kumar, Vineet, Kumar, Rajesh, Shakil, Najam A., Sharma, Sunil K., Prasad, Ashok K., Olsen, Carl Erik, Gupta, Rajendra K., Malhotra, Sanjay V., Van Der Eycken, Erik, Depass, Anthony L., Levon, Kalle, and Parmar, Virinder S.

Published
2010

12. An asymmetric approach towards (-)-aphanorphine and its analogues

Author

KU LEUVEN - Department of Chemistry, Donets, Pavel A., Goeman, Jan L., Van Der Eycken, Johan, Robeyns, Koen, Van Meervelt, Luc, Van Der Eycken, Erik V., KU LEUVEN - Department of Chemistry, Donets, Pavel A., Goeman, Jan L., Van Der Eycken, Johan, Robeyns, Koen, Van Meervelt, Luc, and Van Der Eycken, Erik V.

Abstract

A short enantioselective approach towards the alkaloid (-)-aphanorphine and its substituted analogues is described. The enantiomerically pure starting material for the synthesis was obtained by asymmetric hydrogenation in the presence of the Rh-(S)-PipPhos complex. Microwave-assisted Heck cyclization selectively provided the seven-membered 3-benzazepine ring. Further, the assembly of the tricyclic core of the alkaloid was accomplished by intramolecular radical cyclization. The X-ray structure confirming the absolute configuration of the obtained products is described. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

Published
2009

13. Efficient one-step synthesis of chiral bidentate oxazoline-alcohol ligands via a cyclic imidate ester rearrangement

Author

KU LEUVEN - Department of Chemistry, Noël, Timothy, Robeyns, Koen, Van Meervelt, Luc, Van der Eycken, Erik, Van der Eycken, Johan, KU LEUVEN - Department of Chemistry, Noël, Timothy, Robeyns, Koen, Van Meervelt, Luc, Van der Eycken, Erik, and Van der Eycken, Johan

Abstract

Various chiral bidentate oxazoline-alcohol ligands were obtained in a straightforward one-step synthesis via a cyclic imidate ester rearrangement. These chiral ligands were tested and compared in asymmetric diethylzinc additions to aldehydes resulting in selectivities of up to 87% ee. An interesting chirality switch was observed when a CPh2-tether instead of a CH2 was present, offering the opportunity for dual stereocontrol. © 2009 Elsevier Ltd. All rights reserved.

Published
2009

16. Microwave-assisted, Mo(CO)(6)-mediated, palladium-catalyzed amino-carbonylation of aryl halides using allylamine : from exploration to scale-up

Author

Appukkuttan, Prasad, Axelsson, Linda, Van der Eycken, Erik, Larhed, Mats, Appukkuttan, Prasad, Axelsson, Linda, Van der Eycken, Erik, and Larhed, Mats

Abstract

Palladium-catalyzed aminocarbonylations of various (hetero)aryl halides with allylamine using Mo(CO)(6) as a solid, in situ CO source, were explored. Microwave-enhanced conditions proved to be highly useful in promoting the conversions in a mere 10-20 min with various (hetero)aryl iodides, bromides and chlorides. The scale-up of a microwave-enhanced aminocarbonylation to 25 mmol scale was performed successfully. (C) 2008 Elsevier Ltd. All rights reserved.

Published
2008
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17. Recent developments in microwave-assisted, transition-metal-catalysed C-C and C-N bond-forming reactions

Author

Appukkuttan, Prasad, Van der Eycken, Erik, Appukkuttan, Prasad, and Van der Eycken, Erik

Abstract

A selective over-view of the recent developments of microwave-assisted, transition-metal-catalysed C-C and C-N bond-forming reactions is presented. Microwave-assisted chemistry is a comparatively novel technique in the present-day synthetic world and has recently grown in an exponential manner, stretching from academia to a widely practiced technique in industry. Transition-metal-catalysed C-C and C-N bond-forming reactions represent one of the most interesting and well-investigated type of microwave-assisted reactions, evident from the plethora of available literature and patents in this area. Given the large number of articles published on the subject, we have made a very concise selection from the recent literature, covering manuscripts dealing with the subject from the period of the end 2004 until the first part of 2007.

Published
2008
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18. Microwave-assisted transition-metal-catalyzed synthesis of N-shifted and ring-expanded buflavine analogues

Author

Appukkuttan, Prasad, Dehaen, Wim, Van der Eycken, Erik, Appukkuttan, Prasad, Dehaen, Wim, and Van der Eycken, Erik

Abstract

Two novel and efficient strategies for the synthesis of hitherto unknown N-shifted and ring-expanded buflavine analogues are presented. Construction of the medium-sized ring system of the title molecules, a difficult task due to the high activation energy needed for the ring-closure with the additional rigidity imposed by the biaryl skeleton, was achieved by using Suzuki-Miyaura biaryl coupling and a ring-closing metathesis reaction as the key steps. The combination of a second-generation Grubbs catalyst and microwave irradiation proved to be highly useful in generating the otherwise difficult to obtain medium-sized ring system of the buflavine analogues.

Published
2007
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