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Synlett 2015; 26(11): 1638-1641
DOI: 10.1055/s-0034-1381012
DOI: 10.1055/s-0034-1381012
letter
Chiral Imidazolinium Salts with TIPS Groups for the Palladium-Catalyzed α-Arylation and as Chiral Solvating Agents
Further Information
Publication History
Received: 07 March 2015
Accepted after revision: 16 June 2015
Publication Date:
18 June 2015 (online)


Dedicated to Peter Vollhardt on the occasion of his 69th birthday
Abstract
The synthesis of imidazolinium salts from low-cost amino alcohols incorporating different sterically demanding silyl groups is described. The new salts were analyzed and investigated as carbene precursors in a palladium-catalyzed asymmetric intramolecular α-arylation of an amide. The easily accessible carbene precursors gave enantiomeric excesses of up to 72% with nearly quantitative yields. The salts were also successfully applied as chiral solvating agents with the potassium salt of Mosher’s carboxylate and can therefore contribute to the field of chiral recognition.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1381012.
- Supporting Information