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

被引：26

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

页码：2840 / 2843

页数：4

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