An efficient and practical method for the preparation of α-imidazol-1-yl esters from 1,2-diaza-1,3-dienes (DDs), α-amino esters and aldehydes is described. The overall sequence features a Michael-type conjugate addition between the α-amino ester and the DD, followed by iminium ion formation via condensation with the aldehyde and 1,5-electrocyclization of the resulting thermally-generated azavinyl azomethine ylide to afford eventually α-imidazol-1-yl esters. Such a protocol allows the access to enantiomerically pure imidazoles from optically pure α-amino esters.
α-Aminoester-Derived Imidazoles by 1,5-Electrocyclization of Azavinyl Azomethine Ylides / O. A., Attanasi; Caselli, Emilia; Davoli, Paolo; G., Favi; F., Mantellini; Ori, Claudia; Prati, Fabio. - In: ORGANIC LETTERS. - ISSN 1523-7060. - STAMPA. - 11:13(2009), pp. 2840-2843. [10.1021/ol901051z]
α-Aminoester-Derived Imidazoles by 1,5-Electrocyclization of Azavinyl Azomethine Ylides
CASELLI, Emilia;DAVOLI, Paolo;ORI, CLAUDIA;PRATI, Fabio
2009
Abstract
An efficient and practical method for the preparation of α-imidazol-1-yl esters from 1,2-diaza-1,3-dienes (DDs), α-amino esters and aldehydes is described. The overall sequence features a Michael-type conjugate addition between the α-amino ester and the DD, followed by iminium ion formation via condensation with the aldehyde and 1,5-electrocyclization of the resulting thermally-generated azavinyl azomethine ylide to afford eventually α-imidazol-1-yl esters. Such a protocol allows the access to enantiomerically pure imidazoles from optically pure α-amino esters.
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