HIGHLY STEREOSELECTIVE PREPARATION OF NITRO-OLEFINS AND NITRO-DIENES BY THE ADDITION-ELIMINATION OF COPPER-ZINC ORGANOMETALLICS TO BETA-ALKYLTHIO AND BETA-PHENYLSULFONYL NITRO OLEFINS

被引：32

作者：

RETHERFORD, C ^{[1
]}

KNOCHEL, P ^{[1
]}

机构：

[1] UNIV MICHIGAN,DEPT CHEM,WILLARD H DOW LABS,ANN ARBOR,MI 48109

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 04期

关键词：

D O I：

10.1016/S0040-4039(00)79462-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The addition-elimination of copper-zinc organometallics RCu(CN)ZnX to (E)-1-nitro-2-phenysulfonyl ethylene 2a gave highly functionalized pure (E) nitro olefins and stereoselectively (1E, 3E) and (1E, 3Z)-1-nitrodienes in excellent yields. beta-Alkylthio nitro olefins such as 2-ethylthio-1-nitro-1-cyclohexene 2b and 2,2-dimethylthio-1-nitroethylene 12 were found to have a similar behavior. This methodology allowed an expeditive preparation of the triene 5 which underwent an extremely mild silica gel-catalyzed, stereospecific Diels-Alder cyclization.

引用

页码：441 / 444

页数：4

共 43 条

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