Lewis-acid catalyzed N-acyliminium ion cyclodimerization: synthesis of symmetrical 1,4-dioxanes

被引：5

作者：

Ali, Bakhat ^{[1
]}

Zukerman-Schpector, Julio ^{[2
]}

Ferreira, Fernando P. ^{[3
]}

Shamim, Anwar ^{[4
]}

Pimenta, Daniel C. ^{[5
]}

Stefani, Helici A. ^{[1
,4
]}

机构：

[1] Univ Sao Paulo, Fac Ciencias Farmaceut, Dept Farm, Sao Paulo, SP, Brazil

[2] Univ Fed Sao Carlos, Dept Quim, BR-13560 Sao Carlos, SP, Brazil

[3] Univ Fed Sao Paulo, Dept Biofis, Sao Paulo, SP, Brazil

[4] Univ Sao Paulo, Inst Quim, Sao Paulo, SP, Brazil

[5] Inst Butantan, Sao Paulo, SP, Brazil

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 09期

基金：

巴西圣保罗研究基金会;

关键词：

Amines; N-Acyliminium; Acid catalysis; Cyclodimerization; 1,4-Dioxane; INTERMOLECULAR ADDITION-REACTIONS; ASYMMETRIC-SYNTHESIS; NUCLEOPHILIC-ADDITION; C-2-SYMMETRICAL DIOLS; CYCLIZATION; POTASSIUM; CYCLOPROPANATION; EQUIVALENT; CHEMISTRY;

D O I：

10.1016/j.tetlet.2015.01.059

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The cyclodimerization reaction of N-substituted-5-hydroxy-pyrrolydinones promoted by BF3 center dot Et2O and HCl to obtain symmetrical 1,4-dioxane derivatives was achieved in moderate to good yields, mild conditions, and short reaction times. These transformations render a promising alternative route that provides access to diverse 1,4-dioxane derivatives with a wide structural diversity. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：1153 / 1158

页数：6

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