alpha-Aminoester-Derived Imidazoles by 1,5-Electrocyclization of Azavinyl Azomethine Ylides

作者:Attanasi Orazio A; Caselli Emilia; Davoli Paolo; Favi Gianfranco*; Mantellini Fabio; Ori Claudia; Prati Fabio
来源:Organic Letters, 2009, 11(13): 2840-2843.
DOI:10.1021/ol901051z

摘要

An efficient and practical method for the preparation of alpha-imidazol-1-yl esters from 1,2-diaza-1,3-dienes (DDs), alpha-amino esters, and aldehydes is described. The overall sequence features a Michael-type conjugate addition between the a-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 alpha-imidazol-1-yl esters. Such a protocol allows access to enantiomerically pure Imidazoles from optically pure alpha-amino esters.

  • 出版日期2009-7-2