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

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.

The Room Temperature Organocatalytic Catalytic Synthesis of Chiral Benzopyran[4,3-b]Pyrrole Compounds by 1,3-Dipole Ring Addition Reaction

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 benzopyran4,3-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 benzopyran4,3-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.