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.

Mild synthesis of enantiomerically pure imidazo-[1,2-a]azepines mediated by Yb(OTf)(3)

R. Annunziata
Primo
;
M. Benaglia
Secondo
;
L. Raimondi
Ultimo
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.
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/181598
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