Synthesis of 1,2-dihydropyridines using vinyloxiranes as masked dienolates in imino-aldol reactions

被引：46

作者：

Brunner, Bernhard ^{[1
]}

Stogaitis, Nicole ^{[1
]}

Lautens, Mark ^{[1
]}

机构：

[1] Univ Toronto, Davenport Res Labs, Dept Chem, Toronto, ON M5S 3H6, Canada

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 16期

关键词：

D O I：

10.1021/ol061086p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The application of vinyloxiranes, substituted with an electron-withdrawing group, as masked dienolates in vinylogous imino-aldol reactions was achieved. Under the reaction conditions highly substituted 1,2-dihydropyridines were obtained in moderate to good yields. Mechanistic studies indicate that the reaction proceeds via the formation of an (E)-amino-alpha,beta-unsaturated aldehyde, followed by isomerization to the (Z)-isomer, cyclization, and elimination of a water molecule, leading to the formation of the 1,2-dihydropyridine.

引用

页码：3473 / 3476

页数：4

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