Multicomponent Synthesis of 3(2H)-Furanones Initiated by Copper(II)-Catalyzed Alkyne-Carbonyl Cross Metathesis

被引：0
|
作者：
Su, Zhenjie [1 ]
Wang, Shaozhong [1 ]
机构：
[1] Nanjing Univ, Sch Chem & Chem Engn, State Key Lab Coordinat Chem, Jiangsu Key Lab Adv Organ Mat, 163 Xianlin Ave, Nanjing 210023, Jiangsu, Peoples R China
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2024年 / 30卷 / 48期
基金：
中国国家自然科学基金;
关键词：
Multicomponent annulations; Alkyne-carbonyl metathesis; Cooperative catalysis; 3(2H)-furanone; EFFICIENT SYNTHESIS; BRONSTED ACID; CATALYZED SYNTHESIS; DOMINO REACTION; LEWIS-ACID; KETONES; COPPER; CYCLIZATION; NITRILES; STRATEGY;
D O I：
10.1002/chem.202401999
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The cooperative Lewis and Br & oslash;nsted acid catalysis makes convergent synthesis of 3(2H)-furanones through a three-component coupling of 1,3-diynes, alkyl glyoxylates and water. Control experiments support that Lewis acid-catalyzed highly chemo-, regio- and stereoselective alkyne-carbonyl metathesis of 1,3-diynes and alkyl glyoxylates might be the initial step of this multicomponent annulation. Further chemo- and regioselective hydration of the alkyne-carbonyl metathesis product and subsequent oxa-Michael addition promoted by Br & oslash;nsted acid results in the formation of two C-O bonds of the five-membered oxygen heterocycle.
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页数：6
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