Synthesis of 2-cyclopropyl-4-pyrones and 5-cyclopropyl-2-alkylene-3(2H)-furanones based on tandem cyclization-cyclopropanation strategy

被引：11
|
作者：
Liu, Weishun [1 ,2 ]
Fang, Lin [1 ,2 ]
Wan, Yinbo [1 ,2 ]
Zhang, Jianfang [1 ,2 ]
Deng, Guisheng [1 ,2 ,3 ]
Wang, Jianbo [3 ]
机构：
[1] Hunan Normal Univ, Minist Educ China, Key Lab Chem Biol & Tradit Chinese Med Res, Changsha 410081, Hunan, Peoples R China
[2] Hunan Normal Univ, Key Lab Assembly & Applicat Organ Funct Mol Hunan, Changsha 410081, Hunan, Peoples R China
[3] Peking Univ, BNLMS, Beijing 100871, Peoples R China
来源：
TETRAHEDRON | 2019年 / 75卷 / 07期
基金：
中国国家自然科学基金;
关键词：
4-Pyranone; Alkylene-3(2H)-furanones; Cyclopropanation; Cyclization; Catalysis; Acid; GAMMA-PYRONES; DERIVATIVES; 4-PYRONES; GOLD; 4-PYRIDONE;
D O I：
10.1016/j.tet.2018.11.063
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
In AgSbF6/Rh-2(OAc)(4)/DCE system, two-component diastereoselective reactions of 2-diazo-3,5-dioxo-6-ynoates (phosphonates and sulphones) and alkenes provided easy access to 2-cyclopropyl-gamma-pyrones through 6-endo-dig cyclization-cyclopropanation. In AgOAc/Rh-2(OAc)(4)/Et3N/DCE system, two-component reaction of 2-diazo-3,5-dioxo-7-aryl-6-ynoates and alkenes afforded 2-cyclopropyl-2-alkylene-3(2H)-furanones through 5-exo-dig cyclization-cyclopropanation. The possible mechanism of reaction is discussed. A simple procedure and mild conditions are significant features of this strategy. (C) 2018 Published by Elsevier Ltd.
引用
收藏
页码：855 / 861
页数：7
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