不对称[5+1]串联合成螺[环己酮-氧化吲哚]衍生物  

The Synthesis of Spiro[Cyclohexanone-Oxindoles]Derivatives by Asymmetric[5+1]Cascade

作　　者：杨兰西 李淼 王金娟 陈治明[2] YANG Lanxi;LI Miao;WANG Jinjuan;CHEN Zhiming(School of Chemistry and Materials Science,Guizhou Normal University,Guiyang Guizhou 550001,China;Key Laboratory of Functional Materials Chemistry of Guizhou Province,Guizhou Normal University,Guiyang Guizhou 550001,China)

机构地区：[1]贵州师范大学化学与材料科学学院,贵州贵阳550001 [2]贵州师范大学贵州省功能材料化学重点实验室,贵州贵阳550001

出　　处：《江西师范大学学报（自然科学版）》2022年第3期227-233,共7页Journal of Jiangxi Normal University(Natural Science Edition)

基　　金：国家自然科学基金(21362006)资助项目.

摘　　要：该文报道了一种具有结构复杂性和生物学特性的功能化螺旋吲哚酮的简便合成方法.以二苯乙烯基甲酮和氧化吲哚为原料,用结构上下对称的多氢键型催化剂轴手性胍-酰胺催化不对称串联[5+1]环加成反应,采用一锅法合成了15种螺[环己酮-氧化吲哚]衍生物,并对反应条件进行了优化.研究结果表明:在以物质的量分数20%的手性胍(1a)为催化剂、CH_(2)Cl_(2)为溶剂、在40℃下反应72 h的条件下,以91%的产率、93%的ee值获得螺环己酮吲哚啉酮.The simple synthesis method of functionalized spiral indoleone with complex structure and biological characteristics is reported.Using stilbene ketone and oxindole as raw materials,15 spiro[cyclohexanone-oxyindole]derivatives are synthesized in one pot method by asymmetric cascade[5+1]cycloaddition catalyzed by axial chiral guanidine-amides as a multi-hydrogen bond catalyst with symmetrical structure.The reaction conditions are optimized,and the results show that using 20% mole fraction chiral guanidine 1a as the catalyst,CH_(2)Cl_(2) as the solvent,and reacting at 40℃ for 72 hours,the spirocyclohexanone indolinone is obtained with 91% yield and 93% ee.

关 键 词：吲哚啉酮 不对称串联 [5+1]环加成 螺旋环己烷吲哚啉二酮 

分 类 号：O626.21[理学—有机化学]