SYNTHESIS OF 2(E),4(E)-DIENAMIDES AND 2(E),4(E)-DIENOATES FROM 1,3-DIENES VIA 2-PHENYLSULFONYL 1,3-DIENES

被引：35

作者：

PLOBECK, NA ^{[1
]}

BACKVALL, JE ^{[1
]}

机构：

[1] UNIV UPPSALA,DEPT ORGAN CHEM,BOX 531,S-75121 UPPSALA,SWEDEN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 14期

关键词：

D O I：

10.1021/jo00014a034

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A procedure for the preparation of 2E,4E unsaturated carboxylic acid derivatives from dienes was developed. Transformation of terminal 1,3-dienes to (E)-2-phenylsulfonyl 1,3-dienes and subsequent addition of a carboxy anion equivalent and elimination of benzenesulfinic acid led to 2,4-dienoic amides and esters. In this way the natural products N-isobutyl-2(E)4,(E)-undecadienamide (1a), N-isobutyl-2(E),4(E)-decadienamide (pellitorine, 1b), and methyl 2(E),4(E)-decadienoate (1c) were obtained in high isomeric purity.

引用

页码：4508 / 4512

页数：5

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