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C2轴手性双胍催化叶立德和不饱和吖内酯的串联反应研究
引用本文:张敏,李淼,秦婷,陈治明.C2轴手性双胍催化叶立德和不饱和吖内酯的串联反应研究[J].化学通报,2021,84(5):480-485.
作者姓名:张敏  李淼  秦婷  陈治明
作者单位: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
基金项目:国家自然科学基金项目(21362006)资助
摘    要:本文成功合成了4种基于联二萘酚骨架的手性双胍-酰胺类催化剂,并将其应用于邻羟基苯甲醛亚甲胺叶立德与不饱和吖内酯的1,3-偶极环加成和分子内串联反应。研究表明,在室温下以CHCl_3作为溶剂、轴手性胍(1b,10(mol)%)作为催化剂,反应12h,能以较好的收率(73%~88%)和较高的对映选择性(72%~86%)得到苯并吡喃衍生物。

关 键 词:轴手性胍  1  3-偶极环加成  分子内串联反应
收稿时间:2020/10/13 0:00:00
修稿时间:2020/12/25 0:00:00

Tandem Reaction of Ylide and Unsaturated Azlactone Catalyzed by C2-axis Chiral Biguanide
Zhang Min,Li Miao,Qin Ting,Chen Zhiming.Tandem Reaction of Ylide and Unsaturated Azlactone Catalyzed by C2-axis Chiral Biguanide[J].Chemistry,2021,84(5):480-485.
Authors:Zhang Min  Li Miao  Qin Ting  Chen Zhiming
Institution:College of Chemistry and Materials Science,Guizhou Normal University,Guizhou Provincial Key Laboratory of Functional Materials Chemistry,Guiyang,College of Chemistry and Materials Science,Guizhou Normal University,Guizhou Provincial Key Laboratory of Functional Materials Chemistry,Guiyang,College of Chemistry and Materials Science,Guizhou Normal University,Guizhou Provincial Key Laboratory of Functional Materials Chemistry,Guiyang,College of Chemistry and Materials Science,Guizhou Normal University,Guizhou Provincial Key Laboratory of Functional Materials Chemistry,Guiyang
Abstract:In this paper, four chiral biguanide-amide catalysts based on the BINOL framework were successfully synthesized and applied to the 1,3-dipolar cycloaddition and intramolecular tandem reaction of o-hydroxybenzaldehyde ylide and unsaturated azlactone. Using CHCl3 as the solvent and axial chiral guanidine (1b, 10(mol)%) as the catalyst, reacting at room temperature for 12 hours, a series of benzopyran derivatives can be obtained with good yield (73%~88%) and high enantioselectivity (72%~86%).
Keywords:Axial  chiral guanidine  1  3-Dipole  ring addition  Intramolecular  tandem reaction
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