Efficiency of Acid- and Mercury-Catalyzed Cyclization Reactions in the Synthesis of Tetrahydrofurans from Allylsilyl Alcohols

被引：13

作者：

Pulido, Francisco J. ^{[1
]}

Barbero, Asuncion ^{[1
]}

Val, Patricia ^{[1
]}

Diez, Alberto ^{[1
]}

Gonzalez-Ortega, Alfonso ^{[1
]}

机构：

[1] Univ Valladolid, Dept Organ Chem, E-47011 Valladolid, Spain

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 2012卷 / 27期

关键词：

Synthetic methods; Cyclization; Allenes; Allylic compounds; Oxygen heterocycles; Mercury; SILICON-DIRECTED CYCLIZATION; STEREOSELECTIVE-SYNTHESIS; VINYLSILANES BEARING; ALLENE; SCOPE; CYCLOPROPANATION; CYCLOPENTANE; INDUCTION; STRATEGY; OXO;

D O I：

10.1002/ejoc.201200666

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The scope of the acid-catalyzed and mercury-catalyzed cyclization reactions of allylsilyl alcohols is described. This methodology has been found to be an efficient approach to the synthesis of highly substituted tetrahydrofurans. The stereoselectivity of the cyclization is dependent both on the substitution of the starting alcohol and on the catalyst. A plausible mechanism has been proposed that is consistent with the results.

引用

页码：5350 / 5356

页数：7

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