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

Chem Commun (Camb). 2016 Apr 25;52(32):5516-9. doi: 10.1039/c6cc00784h.

Authors

Zhenghua Li¹, Nandini Sharma¹, Upendra K Sharma¹, Jeroen Jacobs², Luc Van Meervelt², Erik V Van der Eycken¹

Affiliations

¹ Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, B-3001, Leuven, Belgium. usharma81@gmail.com erik.vandereycken@chem.kuleuven.be.
² Biomolecular Architecture, Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, B-3001, Leuven, Belgium.

PMID: 26964634
DOI: 10.1039/c6cc00784h

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Heterocyclic Compounds / chemical synthesis*
Ligands
Palladium / chemistry*

Substances

Heterocyclic Compounds
Ligands
Palladium