Issue 32, 2016
From the journal:

Chemical Communications

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 Meerveltb  and  Erik V. Van der Eycken*a  

* 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.

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

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Article information

DOI
https://doi.org/10.1039/C6CC00784H
Article type
Communication
Submitted
26 Jan 2016
Accepted
02 Mar 2016
First published
02 Mar 2016

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

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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

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