Tetrahedron: Asymmetry

Imidazolinium sulfonate and sulfamate zwitterions as chiral solvating agents for enantiomeric excess calculations

S Tabassum, MA Gilani, R Wilhelm

Index: Tabassum, Sobia; Gilani, Mazhar Amjad; Wilhelm, Rene Tetrahedron Asymmetry, 2011 , vol. 22, # 16-17 p. 1632 - 1639

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Citation Number: 9

Abstract

The synthesis of enantiopure unsymmetrical N-heterocyclic based zwitterions incorporating imidazolinium and alkylsulfonate or sulfamate groups is described. The desired compounds were prepared in good yields from 1, 3-propanesultone or cyclic sulfamidates and imidazolines. The imidazolinium based zwitterions proved to be versatile chiral solvating agents for Mosher's acid, alcohols, cyanohydrins, amino alcohols, nitro alcohols, thiols, ...