(2E,4E)-5-TOSYL-2,4-PENTADIENAMIDES - NEW DIENIC SULFONES FOR THE STEREOSELECTIVE SYNTHESIS OF (2E,4E)-DIENAMIDES

被引：22

作者：

BERNABEU, MC ^{[1
]}

CHINCHILLA, R ^{[1
]}

NAJERA, C ^{[1
]}

机构：

[1] UNIV ALICANTE,FAC CIENCIAS,DEPT QUIM ORGAN,E-03080 ALACANT,SPAIN

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 22期

关键词：

D O I：

10.1016/0040-4039(95)00594-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The iodosulfonylation of (2E)-pentadienamides 1 affords stereoselectively (2E,4E)-5-tosylpentenamides 2. These dienic sulfones suffer nucleophilic vinylic substitution of the tosyl group by sodium thiolates and Grignard reagents to give regio- and stereo-selectively (2E,4E)-dienamides 3. This methodology has been applied to the synthesis of sarmentine (3bg) and an Achillea amide (3cg).

引用

页码：3901 / 3904

页数：4

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