Synthesis of new enantiomerically pure C1- and C2-symmetric N-alkyl-benzimidazolium and thiazolium salts |
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Authors: | Simonetta Orlandi Marinella Caporale Maurizio Benaglia Rita Annunziata |
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Institution: | Dipartimento di Chimica Organica e Industriale, Universita’ degli Studi di Milano, Via Golgi 19, I-20133, Milano, Italy |
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Abstract: | Starting from the commercially available enantiopure (1S,2S)-2-amino-1-phenyl-1,3-propanediol novel enantiomerically pure benzimidazoles were prepared; N-alkylation gave chiral benzimidazolium salts, which were tested in asymmetric benzoin condensations. The synthesis of conceptually new, enantiomerically pure, C2 symmetric bis-thiazolium and bis-benzimidazolium salts was also developed. These new chiral heterocycles were employed as catalysts in the asymmetric dimerisation of benzaldehyde to give benzoin with moderate enantioselectivity. |
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