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.
Synthesis of new enantiomerically pure C-1- and C-2-symmetric N-alkyl-benzimidazolium and thiazolium salts / S. Orlandi, M. Caporale, M. Benaglia, R. Annunziata. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 14:24(2003), pp. 3827-3830. [10.1016/j.tetasy.2003.09.050]
Synthesis of new enantiomerically pure C-1- and C-2-symmetric N-alkyl-benzimidazolium and thiazolium salts
S. OrlandiPrimo
;M. BenagliaPenultimo
;R. AnnunziataUltimo
2003
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.Pubblicazioni consigliate
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