张敏,李淼,秦婷,陈治明.化学通报,2021,84(5):480-485. |
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 |
Tandem Reaction of Ylide and Unsaturated Azlactone Catalyzed by C2-axis Chiral Biguanide |
投稿时间:2020-10-13 修订日期:2020-12-20 |
DOI: |
中文关键词: 轴手性胍 1,3-偶极环加成 分子内串联反应 |
英文关键词:Axial chiral guanidine 1,3-Dipole ring addition Intramolecular tandem reaction |
基金项目:国家自然科学基金项目(21362006)资助 |
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中文摘要: |
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CHCl3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。 |
英文摘要: |
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%). |
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