A Gold-Catalyzed A3 Coupling/Cyclization/Elimination Sequence as Versatile Tool for the Synthesis of Furfuryl Alcohol Derivatives from Glyceraldehyde and Alkynes

被引：32
|
作者：
Li, Jian [1 ,2 ,3 ]
Rudolph, Matthias [1 ]
Rominger, Frank [1 ]
Xie, Jin [1 ]
Hashmi, A. Stephen K. [1 ,4 ]
机构：
[1] Heidelberg Univ, Organ Chem Inst, Neuenheimer Feld 270, D-69120 Heidelberg, Germany
[2] Changzhou Univ, Sch Pharmaceut Engn & Life Sci, 1 Gehu Rd, Changzhou 213164, Peoples R China
[3] Changzhou Univ, Jiangsu Key Lab Adv Catalyt Mat & Technol, 1 Gehu Rd, Changzhou 213164, Peoples R China
[4] King Abdulaziz Univ, Fac Sci, Dept Chem, Jeddah 21589, Saudi Arabia
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2016年 / 358卷 / 02期
关键词：
alcohols; aldehydes; alkynes; amines; furans; gold; FURANS; HETEROCYCLES; ALDEHYDE; AMINES;
D O I：
10.1002/adsc.201500812
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
The reaction of glyceraldehyde with alkynes delivers furfuryl alcohol derivatives within only one reaction step in the presence of a gold(III) catalyst. The reaction cascade is initiated by an intermolecular gold-catalyzed A3 coupling sequence in which morpholine is used as additive. Intramolecular cyclization and subsequent aromatization under elimination of the amine then deliver the target molecules. The protocol offers a valuable alternative to the common routes that are based on functionalization of already existing furan cores.
引用
收藏
页码：207 / 211
页数：5
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