(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

共 36 条

[11] REINVESTIGATION ON THE CATALYTIC ISOMERIZATION OF CARBON-CARBON TRIPLE BONDS [J].

GUO, C ;

LU, XY .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (16) :1921-1923

[12] A FACILE AND HIGHLY STEREOSELECTIVE SYNTHESIS OF (2E)-UNSATURATED, (2E,4E)-UNSATURATED AMIDES AND RELATED NATURAL-PRODUCTS [J].

HUANG, YZ ;

LILAN, S ;

JIANHUA, Y ;

JINGTAO, Z .

TETRAHEDRON LETTERS, 1987, 28 (19) :2159-2162

[13]

JESSUP PJ, ORG SYNTH COLL, V6, P95

[14]

KAGA H, 1994, SYNLETT, P607

[15]

LEWIS N, 1991, SYNLETT, P898

[16]

LIKHITWITAYAWUI.K, 1987, TETRAHEDRON, V43, P3689

[17]

MA DW, 1990, TETRAHEDRON, V46, P3189

[18] HIGHLY STEREOSELECTIVE SYNTHESIS OF (2E,4E)-DIENAMIDES AND (2E,4E)-DIENOATES VIA A DOUBLE ELIMINATION-REACTION [J].

MANDAI, T ;

MORIYAMA, T ;

TSUJIMOTO, K ;

KAWADA, M ;

OTERA, J .

TETRAHEDRON LETTERS, 1986, 27 (05) :603-606

[19] SYNTHESIS OF TRICHONINE VIA DOUBLE ELIMINATION-REACTION AND ITS STRUCTURAL REINVESTIGATION [J].

MORIYAMA, T ;

MANDAI, T ;

KAWADA, M ;

OTERA, J ;

TROST, BM .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (20) :3896-3897

[20] REGIO-SELECTIVE AND STEREO-SELECTIVE SYNTHESIS OF BETA-SULPHONYL-ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS VIA AN IODOSULFONYLATION DEHYDROIODINATION REACTION [J].

NAJERA, C ;

BALDO, B ;

YUS, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (05) :1029-1032

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