摘要
由1,1'-联-2-萘酚经Williamson合成法及与二甘醇/三甘醇单/双对甲苯磺酸酯反应,制得10个联萘(并冠)醚,用氯磺酸磺化,分别得到10个6,6'二磺酸基联萘(并冠)醚(3a～3f,6a～6d).将手性磺酸基联萘(并冠)醚作为Br?nsted酸催化剂,水相中直接催化苯胺、苯甲醛和环己酮三组分Mannich反应,获得高化学收率(90%～99%)和非对映选择性产物,其中(R)-6,6'-二磺酸基联萘并-20-冠-6的非对映选择性de98%.催化苯胺/取代苯胺、苯甲醛和苯乙酮的反应,结果显示反应与催化剂和底物分子结构、反应温度及反应时间有关.催化剂容易回收,重复使用多次活性基本不减.
Ten 6,6＇-disulfobinaphtho-crown ethers were synthesized via sulfonization of the corresponding crown ethers. Chiral sulfobinaphtho-crown ethers were used to catalyze the 3-component Mannich reaction of analine, benzaldehyde and cyclohexanone in aqueous media and show excellent yield and diastereoselec- tivity up to de 98%. Investigation into the reactions of analine/substituted analine, benzaldehyde and hyp- none demonstrates that the molecular structures of the catalysts and the substrate compounds, as well as the reaction temperature and time can influence the catalytic results.
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
2007年第4期488-493,共6页
Chinese Journal of Organic Chemistry
基金
广东省科技计划(No.2003C104030)资助项目.
