摘要
A series of new chiral amide ligands were prepared from natural amino acids and applied to the copper-catalyzed asymmetric oxidative homocoupling reaction of 3-hydroxy-2-naphthoates.By optimizing the reaction conditions,it was found that when using L3(5 mol%)as the ligand,CuCl(5 mol%)as the catalyst,dichloromethane as the solvent,2,2,6,6-tetramethylpiperidine 1-oxyl(TEMPO)/O2 as the oxidant,and under the reaction condition of 40℃,this method exhibited good substrate tolerance.Under these conditions,a series of chiral 1,1'-bi-2-naphthol(BINOL)derivatives were synthesized with yields of 45%~90%and enantioselectivities ranging from 50∶50 to 97∶3.
以天然氨基酸为原料,制备了一系列新型手性酰胺类配体,并将其与铜盐原位配位,用于催化3-羟基-2-萘酸酯的不对称氧化自偶联反应.通过对反应条件的系统优化,发现在以L3(5 mol%)为配体,CuCl(5 mol%)为催化剂,二氯甲烷为溶剂,2,2,6,6-四甲基哌啶氧化物(TEMPO)/O2为氧化剂,40℃的反应条件下,该方法表现出良好的底物耐受性,以45%~90%的产率和50∶50~97∶3的对映选择性合成了一系列手性1,1'-联二萘酚(BINOL)衍生物.
出处
《有机化学》
北大核心
2026年第1期167-180,共14页
Chinese Journal of Organic Chemistry
基金
国家自然科学基金(No.22201186)
石河子大学高层次人才启动基金(No.2022ZK005)
新疆维吾尔自治区天池英才计划资助项目.
