A NEW METHOD FOR THE STEREOCONTROLLED SYNTHESIS OF SILYL DIENOL ETHERS USING (NAPHTHALENE)CHROMIUM TRICARBONYL CATALYZED ISOMERIZATION

被引：80

作者：

SODEOKA, M ^{[1
]}

YAMADA, H ^{[1
]}

SHIBASAKI, M ^{[1
]}

机构：

[1] HOKKAIDO UNIV,FAC PHARMACEUT SCI,SAPPORO,HOKKAIDO 060,JAPAN

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1990年 / 112卷 / 12期

关键词：

D O I：

10.1021/ja00168a041

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Various tert-butyldimethylsilyl dienol ethers of type 4 were synthesized in a highly stereoselective manner for the first time. Treatment of (1Z)-1-[[(tert-butyldimethylsilyl)oxy] methyl] butadiene derivatives 1 with 20 mol% of (naphthalene) Cr(CO)3 in degassed acetone at 20 °C provided silyl dienol ethers 4 exclusively in nearly quantitative yields. In order to demonstrate synthetic utility of silyl dienol ethers of this type, the intermolecular Diels-Alder reaction of 7 with Nphenylmaleimide in the presence of a small amount of K2CO3 was carried out to give the endo Diels-Alder adduct 20 as the sole product. Furthermore, application to the intramolecular Diels-Alder reaction was also undertaken, giving the endo Diels-Alder adduct (the cis-hydrindan derivative) 25, exclusively. © 1990, American Chemical Society. All rights reserved.

引用

页码：4906 / 4911

页数：6

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