The reaction of various chiral 2,2'-diaryldialdehydes with achiral and chiral 1,2-diamines in the presence of Lewis acids to give imidazo[1,2-a]azepines was investigated. Best results were achieved with Yb(OTf)(3); the reaction outcome is strongly dependent upon the geometric features of both reactants. Kinetic resolution of rac-2,2'-dinaphthyldialdehyde with (R,R)-1,2-diphenyl-1,2-diamminoethane (up to 92% e.e.) was achieved. (C) 2001 Elsevier Science Ltd. All rights reserved.
Mild synthesis of enantiomerically pure imidazo-[1,2-a]azepines mediated by Yb(OTf)(3) / R. Annunziata, M. Benaglia, L. Raimondi. - In: TETRAHEDRON. - ISSN 0040-4020. - 57:52(2001), pp. 10357-10363. [10.1016/S0040-4020(01)01078-X]
Mild synthesis of enantiomerically pure imidazo-[1,2-a]azepines mediated by Yb(OTf)(3)
R. AnnunziataPrimo
;M. BenagliaSecondo
;L. RaimondiUltimo
2001
Abstract
The reaction of various chiral 2,2'-diaryldialdehydes with achiral and chiral 1,2-diamines in the presence of Lewis acids to give imidazo[1,2-a]azepines was investigated. Best results were achieved with Yb(OTf)(3); the reaction outcome is strongly dependent upon the geometric features of both reactants. Kinetic resolution of rac-2,2'-dinaphthyldialdehyde with (R,R)-1,2-diphenyl-1,2-diamminoethane (up to 92% e.e.) was achieved. (C) 2001 Elsevier Science Ltd. All rights reserved.
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