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

被引：27
作者：
Attanasi, Orazio A. [1 ]
Caselli, Emilia [2 ]
Davoli, Paolo [2 ]
Favi, Gianfranco [1 ]
Mantellini, Fabio [1 ]
Ori, Claudia [2 ]
Prati, Fabio [2 ]
机构：
[1] Univ Urbino Carlo Bo, Ist Chim Organ, I-61029 Urbino, Italy
[2] Univ Modena & Reggio Emilia, Dipartimento Chim, I-41100 Modena, Italy
来源：
ORGANIC LETTERS | 2009年 / 11卷 / 13期
关键词：
ONE-POT; CYCLOADDITION; 1,2-DIAZA-1,3-BUTADIENES; PROTOCOL; PYRROLES; AMINES; ACIDS;
D O I：
10.1021/ol901051z
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
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.
引用
收藏
页码：2840 / 2843
页数：4
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