3,3′-二取代联二萘酚硫脲催化合成4H-吡喃衍生物  

Syntheses of 4H-Pyran Derivatives Catalyzed by 3,3′-Disubstituted BINOL Thiourea

作　　者：安雪婕 李淼 秦婷 陈治明 An Xuejie;Li Miao;Qin Ting;Chen Zhiming(School of Chemistry and Materials Science,Guizhou Normal University,Guizhou Key Laboratory of Functional Materials Chemistry,Guiyang,550001)

机构地区：[1]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,贵阳550001

出　　处：《化学通报》2021年第3期273-278,共6页Chemistry

基　　金：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%。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%.

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 

分 类 号：O626[理学—有机化学]