[1]甘 坤,李 淼,刘 莉,等.室温有机催化1,3-偶极环加成反应合成苯并吡喃[4,3-b]吡咯类化合物[J].江西师范大学学报(自然科学版),2022,(05):489-496.[doi:10.16357/j.cnki.issn1000-5862.2022.05.08]
 GAN Kun,LI Miao,LIU Li,et al.The Room Temperature Organocatalytic Catalytic Synthesis of Chiral Benzopyran[4,3-b]Pyrrole Compounds by 1,3-Dipole Ring Addition Reaction[J].Journal of Jiangxi Normal University:Natural Science Edition,2022,(05):489-496.[doi:10.16357/j.cnki.issn1000-5862.2022.05.08]
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室温有机催化1,3-偶极环加成反应合成苯并吡喃[4,3-b]吡咯类化合物()
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《江西师范大学学报》(自然科学版)[ISSN:1006-6977/CN:61-1281/TN]

卷:
期数:
2022年05期
页码:
489-496
栏目:
化学
出版日期:
2022-09-25

文章信息/Info

Title:
The Room Temperature Organocatalytic Catalytic Synthesis of Chiral Benzopyran[4,3-b]Pyrrole Compounds by 1,3-Dipole Ring Addition Reaction
文章编号:
1000-5862(2022)05-0489-08
作者:
甘 坤李 淼刘 莉陈治明*
(贵州师范大学化学与材料科学学院,贵州省功能材料化学重点实验室,贵州 贵阳 550001)
Author(s):
GAN KunLI MiaoLIU LiCHEN Zhiming*
(Key Laboratory of Functional Materials Chemistry of Guizhou Province,College of Chemistry and Materials Science,Guizhou Normal University,Guiyang Guizhou 550001,China)
关键词:
13-偶极环加成 不对称催化 苯并吡喃[43-b]吡咯
Keywords:
13-dipole ring addition asymmetric catalysis benzopyran[43-b] pyrrole
分类号:
O 626
DOI:
10.16357/j.cnki.issn1000-5862.2022.05.08
文献标志码:
A
摘要:
该文设计合成了(1R)-2,2'-二羟基-N,N'-双((2-甲基环己基)氨基甲硫酰基)[1,1'-联萘]-3,3'-二甲酰胺(1a)等4种催化剂,并将其用于不对称催化亚甲胺叶里德的1,3-偶极环加成反应合成苯并吡喃[4,3-b]吡咯化合物.实验结果表明:在室温下,以物质的量分数为10%的1d作为催化剂,以CH2Cl2为溶剂,苯并吡喃[4,3-b]吡咯化合物的产率(88%)较高,且产物具有较高(86%)的对映选择性.该反应具有环境友好、反应条件温和、催化剂经济易得和操作简单等优点.
Abstract:
Four catalysts,including(1R)-2,2'-dihydroxy-N,N'-bis(2-methylcyclohexyl)carbamate)-[1,1'-binaphthal]-3,3'-dicarboxamide 1a,are successfully designed and synthesized,and they are used to asymmetrically catalyze the 1,3-dipole ring addition reaction of methyleneamine Yelide to synthesize benzopyran[4,3-b] pyrrole compounds.The experimental results show that at room temperature of 25 ℃,10 mol% 1d as the catalyst,the solvent is CH2Cl2,and the synthesized benzopyran[4,3-b] pyrrole compound obtains good yield(88%)and high enantioselectivity(86%).The reaction offers the advantages of environmental friendliness,mild reaction conditions, economical and easy catalyst operation.

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备注/Memo

备注/Memo:
收稿日期:2022-05-06
基金项目:国家自然科学基金(21362006)资助项目.
通信作者:陈治明(1971—),男,贵州贵阳人,教授,主要从事有机合成研究.E-mail:czm000219@163.com
更新日期/Last Update: 2022-09-25