Acid-mediated coupling of γ-hydroxybutenolides and aldehydes: synthesis of a new class of spirocyclic ketal-lactones

被引：10
|
作者：
Munoz, Alberto [1 ]
Murelli, Ryan P. [1 ,2 ]
机构：
[1] CUNY Brooklyn Coll, Dept Chem, Brooklyn, NY 11210 USA
[2] CUNY, Grad Ctr, Dept Chem, New York, NY 10016 USA
来源：
TETRAHEDRON LETTERS | 2012年 / 53卷 / 50期
基金：
美国国家科学基金会; 美国国家卫生研究院;
关键词：
Spirocycles; Prins reaction; gamma-Hydroxybutenolides; DIELS-ALDER CYCLOADDITIONS; 5-METHYLENE-2(5H)-FURANONE; BUTENOLIDES; SELECTIVITY; CARBON;
D O I：
10.1016/j.tetlet.2012.09.139
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
In the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf), gamma-methyl-gamma-hydroxybutenolide reacts with aromatic aldehydes to generate a new class of stereochemically rich spirocyclic ketal-lactones in good yields and with excellent stereoselectivities. We believe that this process takes place through the in situ generation of protoanemonin followed by a Prins reaction. Herein, we describe this discovery, along with substrate scope and preliminary mechanistic studies. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6779 / 6781
页数：3
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