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Synthesis 2021; 53(14): 2512-2516
DOI: 10.1055/a-1404-4966
DOI: 10.1055/a-1404-4966
paper
The Trityl Cation Embedded into a [7]Helicene-Like Backbone: Preparation and Application as a Lewis Acid Catalyst
M.O. is indebted to the Einstein Foundation (Berlin) for an endowed professorship.
Abstract
The synthesis of a helically chiral carbenium ion is reported. The new motif is essentially a trityl cation embedded into a [7]helicene-like framework. The key step in its preparation establishes the π-extended fluorenone system in one step by an unprecedented palladium-catalyzed carbonylative annulation of a 4,4′-biphenanthryl-3,3′-diyl precursor. The racemic form of the new carbon Lewis acid was found to catalyze a representative set of reactions typically promoted by the trityl cation.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1404-4966.
- Supporting Information
Publication History
Received: 31 January 2021
Accepted: 03 March 2021
Accepted Manuscript online:
03 March 2021
Article published online:
11 March 2021
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For a comprehensive study, see:
For Mukaiyama’s seminal work, see:
For work from the Franzén group, see:
As an alternative approach, carbenium ions can be paired with chiral counteranions. Adduct formation can, however, lower the reactivity of the carbon Lewis acid. For key publications, see:
See also:
For related palladium-catalyzed approaches to the fluorenone skeleton, see:
For experimental results on the racemization of specific [7]helicene derivatives, see the Supporting Information of reference 14. For selected studies on the racemization of helicenes, see: