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Literature DB >> 24737692

Asymmetric catalysis on the nanoscale: the organocatalytic approach to helicenes.

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

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.

Entities: Chemical

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

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Substances：

Year: 2014 PMID： 24737692 DOI： 10.1002/anie.201400474

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

4 in total

1. Gas phase synthesis of [4]-helicene.

Authors: Long Zhao; Ralf I Kaiser; Bo Xu; Utuq Ablikim; Wenchao Lu; Musahid Ahmed; Mikhail M Evseev; Eugene K Bashkirov; Valeriy N Azyazov; Marsel V Zagidullin; Alexander N Morozov; A Hasan Howlader; Stanislaw F Wnuk; Alexander M Mebel; Dharati Joshi; Gregory Veber; Felix R Fischer
Journal: Nat Commun Date: 2019-04-03 Impact factor: 14.919

Asymmetric catalysis on the nanoscale: the organocatalytic approach to helicenes.

1. Gas phase synthesis of [4]-helicene.

2. Homologation of the Fischer Indolization: A Quinoline Synthesis via Homo-Diaza-Cope Rearrangement.

3. Synthesis, crystal structures and properties of carbazole-based [6]helicenes fused with an azine ring.

4. Crystal structure of 5,15-dihexyl-5,15-di-hydro-benzo[2,1-b:4,3-c']dicarbazole hexane 0.375-solvate.