Ligand-controlled product selectivity in palladium-catalyzed domino post-Ugi construction of (spiro)polyheterocycles

Zhenghua Li; Nandini Sharma; Upendra K. Sharma; Jeroen Jacobs; Luc Van Meervelt; Erik V. Van der Eycken

doi:10.1039/C6CC00784H

Ligand-controlled product selectivity in palladium-catalyzed domino post-Ugi construction of (spiro)polyheterocycles

Zhenghua Li,^a Nandini Sharma,^a Upendra K. Sharma,*^a Jeroen Jacobs,^b Luc Van Meervelt^b and Erik V. Van der Eycken*^a

Author affiliations

* Corresponding authors

^a Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, Leuven, Belgium
E-mail: usharma81@gmail.com, erik.vandereycken@chem.kuleuven.be

^b Biomolecular Architecture, Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, Leuven, Belgium

Abstract

A novel diversity-oriented access to (spiro)polyheterocycles possessing two adjacent quaternary carbon stereocenters is described. By combining an Ugi 4-CR with Pd-catalysis, the possible mode of cyclization is controlled by the appropriate choice of ligands. Using XantPhos, spirooxindoles are selectively generated, while with BINAP fused polycyclic cis-dihydrobenzofurans are obtained with high diastereoselectivity.

Supplementary files

Publication details

The article was received on 26 Jan 2016, accepted on 02 Mar 2016 and first published on 02 Mar 2016

Article type: Communication

DOI: 10.1039/C6CC00784H

Citation: Chem. Commun., 2016,52, 5516-5519

Request permissions
Ligand-controlled product selectivity in palladium-catalyzed domino post-Ugi construction of (spiro)polyheterocycles

Z. Li, N. Sharma, U. K. Sharma, J. Jacobs, L. Van Meervelt and E. V. Van der Eycken, Chem. Commun., 2016, 52, 5516
DOI: 10.1039/C6CC00784H
If you are not the author of this article and you wish to reproduce material from it in a third party non-RSC publication you must formally request permission using RightsLink. Go to our Instructions for using RightsLink page for details.

Authors contributing to RSC publications (journal articles, books or book chapters) do not need to formally request permission to reproduce material contained in this article provided that the correct acknowledgement is given with the reproduced material.

Reproduced material should be attributed as follows:
For reproduction of material from NJC:
Reproduced from Ref. XX with permission from the Centre National de la Recherche Scientifique (CNRS) and The Royal Society of Chemistry.

For reproduction of material from PCCP:
Reproduced from Ref. XX with permission from the PCCP Owner Societies.

For reproduction of material from PPS:
Reproduced from Ref. XX with permission from the European Society for Photobiology, the European Photochemistry Association, and The Royal Society of Chemistry.

For reproduction of material from all other RSC journals and books:
Reproduced from Ref. XX with permission from The Royal Society of Chemistry.
If the material has been adapted instead of reproduced from the original RSC publication "Reproduced from" can be substituted with "Adapted from".

In all cases the Ref. XX is the XXth reference in the list of references.

If you are the author of this article you do not need to formally request permission to reproduce figures, diagrams etc. contained in this article in third party publications or in a thesis or dissertation provided that the correct acknowledgement is given with the reproduced material.

Reproduced material should be attributed as follows:
For reproduction of material from NJC:
[Original citation] - Reproduced by permission of The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC

For reproduction of material from PCCP:
[Original citation] - Reproduced by permission of the PCCP Owner Societies

For reproduction of material from PPS:
[Original citation] - Reproduced by permission of The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC

For reproduction of material from all other RSC journals:
[Original citation] - Reproduced by permission of The Royal Society of Chemistry
If you are the author of this article you still need to obtain permission to reproduce the whole article in a third party publication with the exception of reproduction of the whole article in a thesis or dissertation.

Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Chemical Communications

Ligand-controlled product selectivity in palladium-catalyzed domino post-Ugi construction of (spiro)polyheterocycles

Abstract

Supplementary files

Publication details

Ligand-controlled product selectivity in palladium-catalyzed domino post-Ugi construction of (spiro)polyheterocycles

Search articles by author

Spotlight

Advertisements