Iodine-Catalyzed Prins Cyclization of Aliphatic and Aromatic Ketones

被引：3

作者：

Reddy, K. R. Kishore K. ^{[1
]}

Silva, Luiz F., Jr. ^{[1
]}

机构：

[1] Univ Sao Paulo, Inst Quim, Dept Quim Fundamental, BR-05513970 Sao Paulo, Brazil

来源：

JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY | 2013年 / 24卷 / 09期

基金：

巴西圣保罗研究基金会;

关键词：

iodine; Prins cyclization; ketones; pyrans; spiro compounds; DIASTEREOSELECTIVE SYNTHESIS; ANTIPROLIFERATIVE ACTIVITY; EXPEDITIOUS SYNTHESIS; MACROCYCLIZATION; NEOPELTOLIDE; DERIVATIVES; ANALOGS;

D O I：

10.5935/0103-5053.20130178

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Iodine-catalyzed Prins cyclization of homoallylic alcohols and ketones was investigated. Anhydrous conditions and inert atmosphere are not required in this metal-free protocol. The reaction of 2-(3,4-dihydronaphthalen-1-yl)propan-1-ol with six aliphatic symmetric ketones gave the desired products in 67-77% yield. Cyclization was performed with four aliphatic unsymmetric ketones, leading to corresponding pyrans in 66-76% yield. Prins cyclization was also accomplished with four aromatic ketones in 37-66% yield. Finally, Prins cyclization of the monoterpene isopulegol and acetone was successfully achieved.

引用

页码：1414 / U132

页数：28

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