Siloxacyclopentenes as Dienophile-Linked Directing Groups in Intramolecular Diels-Alder Reactions

被引：15

作者：

Halvorsen, Geoff T. ^{[1
]}

Roush, William R. ^{[1
]}

机构：

[1] Scripps Florida, Dept Chem, Jupiter, FL 33458 USA

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 22期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1021/ol802266s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis and intramolecular Diels-Alder reactions of trienes 5 and 6 with a siloxacyclopentene-constrained dienophile are described. These reactions provide the primary cycloadducts 7 and 8 with high diastereoselectivity. These cycloadducts possess trans-relationships between the ring fusion proton and the adjacent C(1) alkoxy group and can be further elaborated to alcohols 9 and 11 (via protiodesilylation) or to 10 and 12 (via Fleming-Tamao oxidation) depending on the substitutent R.

引用

页码：5313 / 5316

页数：4

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