Catalytic Arene-forming Aldol Condensation: Stereoselective Synthesis of Rotationally Restricted Aromatic Compounds

Authors

  • Vincent C. Fäseke University of Basel Department of Chemistry St. Johanns-Ring 19 CH-4056 Basel, Switzerland
  • Reto M. Witzig University of Basel Department of Chemistry St. Johanns-Ring 19 CH-4056 Basel, Switzerland
  • Achim Link University of Basel Department of Chemistry St. Johanns-Ring 19 CH-4056 Basel, Switzerland
  • Dominik Lotter University of Basel Department of Chemistry St. Johanns-Ring 19 CH-4056 Basel, Switzerland
  • Christof Sparr University of Basel Department of Chemistry St. Johanns-Ring 19 CH-4056 Basel, Switzerland. christof.sparr@unibas.ch

DOI:

https://doi.org/10.2533/chimia.2017.596

Keywords:

Aldol condensation, Arylenes, Atropisomers, Axial chirality, Stereoselective catalysis

Abstract

By taking inspiration from the fascinating biosynthetic machinery that creates aromatic polyketides, our group investigates analogous reactions catalyzed by small molecules. We are particularly captivated by the prospects of intramolecular aldol condensation reactions to generate different rotationally restricted aromatic compounds. In a first project of our independent research group, a highly stereoselective amine catalyzed synthesis of axially chiral biaryls, tertiary aromatic amides and oligo-1,2-naphthylenes has been developed. In this article, we outline the twists and turns for our escape from the aromatic flatland to structurally intriguing chiral arene scaffolds relevant for various fields of application.

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Published

2017-09-27

Issue

Section

Scientific Articles