Asymmetric catalysis on the nanoscale: the organocatalytic approach to helicenes

Lisa Kötzner; Matthew J Webber; Alberto Martínez; Claudia De Fusco; Benjamin List

doi:10.1002/anie.201400474

Asymmetric catalysis on the nanoscale: the organocatalytic approach to helicenes

Angew Chem Int Ed Engl. 2014 May 12;53(20):5202-5. doi: 10.1002/anie.201400474. Epub 2014 Apr 15.

Authors

Lisa Kötzner¹, Matthew J Webber, Alberto Martínez, Claudia De Fusco, Benjamin List

Affiliation

¹ Max-Planck-Institut für Kohlenforschung, Kaiser Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany).

PMID: 24737692
DOI: 10.1002/anie.201400474

Abstract

The first asymmetric organocatalytic synthesis of helicenes is reported. A novel SPINOL-derived phosphoric acid, bearing extended π-substituents, catalyzes the asymmetric synthesis of helicenes through an enantioselective Fischer indole reaction. A variety of azahelicenes and diazahelicenes could be obtained with good to excellent yields and enantioselectivities.

Keywords: Brønsted acid catalysis; Fischer indole synthesis; helicenes; organocatalysis.

Publication types

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

MeSH terms

Catalysis
Nanotechnology*
Organic Chemicals / chemistry*
Polycyclic Compounds / chemistry*

Substances

Organic Chemicals
Polycyclic Compounds
helicenes