手性金属磷酸盐催化2-萘酚与亚胺不对称反应

Chiral metal phosphate catalyzes asymmetric reaction of naphthol and imine

摘要:

以2,6-二异丙基-4-金刚烷基苯取代的BINOL骨架磷酸镁盐作为催化剂，催化2-萘酚与N-(叔丁氧羰基)-苯甲醛亚胺（Ⅲa）的不对称反应。在常温、反应时间15 h、甲苯作溶剂、催化剂用量5%（以底物的物质的量为基准，下同）的条件下，反应生成的叔丁基（2-羟基萘-1-基）（苯基）氨基甲酸甲酯（Ⅳa）达到97%的产率和90%的对映选择性。用1HNMR和HPLC对产物进行了表征。对反应条件进行了优化，确定了催化剂、反应时间、溶剂、反应温度等关键参数。此催化方法能使用少量的催化剂进行高效催化，且反应条件温和，经济高效，绿色环保。

Abstract:

Using 2,6-(Isopropyl)2-4-Adamantyl-C6H2 substituted BINOL skeleton magnesium phosphate as catalyst, to catalyze the asymmetric reaction of 2-naphthol and tert-Butyl benzylidenecarbamate(Ⅲa). Under the conditions of room temperature, reaction time of 15 h, toluene as solvent, and the amount of catalyst is 5% (based on the amount of substrate material, the same below), the tert-butyl (2-hydroxynaphth-1-yl)(phenyl)methylcarbamate(Ⅳa) produced by the reaction reached 97% yield and 90% enantioselectivity. Characterization using 1HNMR and HPLC. This study optimized the reaction conditions and determined the key parameters such as catalyst, reaction time, solvent, and reaction temperature. A small amount of catalyst can efficiently catalyze the reaction. The reaction condition is mild. And the method is cost-effective and environmentally friendly.