Synlett 2015; 26(11): 1638-1641
DOI: 10.1055/s-0034-1381012
letter
© Georg Thieme Verlag Stuttgart · New York

Chiral Imidazolinium Salts with TIPS Groups for the Palladium-Catalyzed α-Arylation and as Chiral Solvating Agents

Mazhar Amjad Gilani
,
Eduard Rais
,
René Wilhelm*
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Publication History

Received: 07 March 2015

Accepted after revision: 16 June 2015

Publication Date:
18 June 2015 (online)


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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.

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