摘要
从L-脯氨酸衍生而来的酰胺膦类化合物1,经脱去保护基得到的氨基膦2,用正丁基锂处理后,用2-甲氧基吡啶类化合物捕获,得到一类吡啶型的手性N,P-配体4;氨基醇与碳酸二乙酯生成的噁唑啉酮6,与四氟硼酸三乙氧基鎓盐反应制得的乙氧基噁唑啉7直接与氨基膦2反应,合成了噁唑啉型手性N,P-配体8.将两类手性N,P-配体应用于Ag(I)催化的1,3-偶极环加成反应,通过对反应条件进行优化,发现手性N,P-配体与AgOTf所形成的催化剂能很好地催化1,3-偶极环加成反应,最高可以以93%的收率获得环加成产物,ee值最高可以达到15%.
Aminophosphine 2 was obtained by deprotection of amidophosphine 1, which was derived from L-proline. Depro- tonation of aminophosphine 2 with n-BuLl, and then being captured by 2-MeO-pyridine gave chiral pyridyl N,P-ligands 4. Reaction of aminoalcohol and diethyl carbonate afforded oxazolidione 6, which was converted to compounds 7 by the reaction with triethyloxonium tetrafluoroborate. Chiral N,P-ligands 8 were obtained by the reaction of compounds 7 with amino- phosphine 2. Two kinds of chiral N,P-ligands shown excellent catalytic activity in Ag（I） catalytic asymmetric 1,3-dipolar cvcloaddition, and up to 93%0 yield and 15% ee were obtained.
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
2013年第4期848-853,共6页
Chinese Journal of Organic Chemistry
基金
国家自然科学基金(No.20902015)
中央高校基础研究基金(No.2010055)资助项目~~
