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
收藏
页码：1414 / U132
页数：28
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