摘要
采用3-(4-三氟甲基苯亚甲基)吲哚啉-2-酮和2-(4-三氟甲基苯亚甲基)-1H-茚-1,3(2H)-二酮分别与鉮盐在二氯甲烷中,碳酸钾或氟化钾存在下反应,可高产率、高立体选择性地得到以反式构型为主的含三氟甲基的3'-螺环丙基取代的氧化吲哚和2'-螺环丙基取代的茚二酮衍生物.产物相对构型经X射线单晶衍射或1H-1H NOESY谱确定.还从反应机理的角度对产物构型做了解释.
In this paper,the new synthesis of trans-2,3-dihydro-spiro[cyclopropane-1,3＇-indolin]-2＇-one and trans-2,3-dihydro-spiro[cyclopropane-1,2＇-indane]-1＇,3＇-dione containing CF3 group was reported.Arsonium bromides 2 reacted with 2-（4-（trifluoromethyl）benzylidene）-1H-indene-1,3（2H）-dione（1） or 3-（4-（trifluoro-methyl）benzylidene）indolin-2-one（3）,using KF or K2CO3 as base in CH2Cl2,to provide the target products with high stereoselectivity in good yields.The relative stereochemistry of key compounds has been determined by single-crystal X-ray structural analysis and 1H-1H NOESY technique.The mechanism was also proposed.
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
2010年第10期1521-1528,共8页
Chinese Journal of Organic Chemistry
基金
国家自然科学基金(Nos.20872088
20802043)
上海市教委重点学科(No.J50102)资助项目
关键词
螺环丙基
氧化吲哚
茚二酮
胂叶立德
立体选择性合成
spirocyclopropyl
oxindole
1
3-indandione
arsonium ylide
stereoselective synthesis
