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3,3'-二取代联二萘酚硫脲催化合成4H-吡喃衍生物
引用本文:安雪婕,李淼,秦婷,陈治明.3,3'-二取代联二萘酚硫脲催化合成4H-吡喃衍生物[J].化学通报,2021,84(3):273-278.
作者姓名:安雪婕  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,贵州师范大学 化学与材料科学学院,贵州师范大学 化学与材料科学学院,贵州师范大学 化学与材料科学学院
基金项目:国家自然科学基金项目(21362006)资助
摘    要:合成了3种3,3′-二取代BINOL轴手性硫脲类催化剂(3a~3c),并成功地将其应用于催化不对称Knoevenagel-Micheal的串联反应。结果表明,以CH2Cl2为溶剂、3a为催化剂各种取代芳香醛与丙二腈和1,3-环己二酮在25℃下反应得到4H-吡喃衍生物,产率可达98%,对映选择性高达94%。

关 键 词:4H-吡喃衍生物  Knoevenagel-Micheal串联反应  3  3′-二取代BINOL  硫脲类催化剂
收稿时间:2020/7/21 0:00:00
修稿时间:2020/9/1 0:00:00

Syntheses of 4H-Pyran Derivatives Catalyzed by 3,3'-Disubstituted BINOL Thiourea
An Xuejie,Li Miao,Qin Ting,Chen Zhiming.Syntheses of 4H-Pyran Derivatives Catalyzed by 3,3'-Disubstituted BINOL Thiourea[J].Chemistry,2021,84(3):273-278.
Authors:An Xuejie  Li Miao  Qin Ting  Chen Zhiming
Institution:School of chemistry and materials science,Guizhou Normal University,Guizhou Key Laboratory of Functional Materials Chemistry,School of chemistry and materials science,Guizhou Normal University,Guizhou Key Laboratory of Functional Materials Chemistry,School of chemistry and materials science,Guizhou Normal University,Guizhou Key Laboratory of Functional Materials Chemistry,School of chemistry and materials science,Guizhou Normal University,Guizhou Key Laboratory of Functional Materials Chemistry
Abstract:Three 3,3′-disubstituted BINOL axial chiral thiourea catalysts(3 a~3 c)were synthesized and successfully applied to asymmetric Knoevenagel Micheal series reaction to synthesize a series of 4H-pyran derivatives.The results showed that the reaction of various substituted aromatic aldehydes with malononitrile and 1,3-cyclohexanedione at 25℃using CH2Cl2 as solvent and 3 a as the catalyst gave 4H-pyran derivatives with a yield of 98%,enantioselectivity up to 94%.
Keywords:4H-pyran derivative  Knoevenagel Michael series reaction  3  3''-disubstituted BINOL  Thiourea catalysts
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