Mild synthesis of enantiomerically pure imidazo-[1,2-a]azepines mediated by Yb(OTf)3 |
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| Authors: | Rita Annunziata Maurizio Benaglia Laura Raimondi |
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| Institution: | Dipartimento di Chimica Organica e Industriale and Centro CNR, Università di Milano, Dipartimento di Chimica Organica e Industriale and Centro CNR Studio, Sintesi Stereochimica Speciali Sistemi Organici, via Camillo Golgi 19, I-20133 Milano, Italy |
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| Abstract: | The reaction of various chiral 2,2′-diaryldialdehydes with achiral and chiral 1,2-diamines in the presence of Lewis acids to give imidazo1,2-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. |
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| Keywords: | imidazo[1 2-a]azepines ytterbium triflate imine kinetic resolution |
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