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Alpha-aminoester-derived imidazoles by 1,5-electrocyclization of azavinyl azomethine ylides.
- Source :
-
Organic letters [Org Lett] 2009 Jul 02; Vol. 11 (13), pp. 2840-3. - Publication Year :
- 2009
-
Abstract
- 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 alpha-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.
Details
- Language :
- English
- ISSN :
- 1523-7052
- Volume :
- 11
- Issue :
- 13
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 19514726
- Full Text :
- https://doi.org/10.1021/ol901051z