新型含脯氨酚母核手性催化剂的设计、合成及应用研究

Design、synthesis and application of new chiral catalysts were very immportant in asymmetric organic chemistry.This project was planned to synthetize a new kinds of catalysts or ligands which have a pyrrolidine as the functional group and a BINOL scaffold as the chiral environment.This kinds of catalysts or ligands not only has a C2 axial chirality but also a centre chirality and we named Py-Binol. Based on Py-Binol core sacffold, a series of chiral catalysts or ligangds can be prepared such as chiral DMAP. The first research of this peoject was planed to examine the application of Py-Binol and its derivatives in chiral recognization for carboxylic acids, particularly amino acids, and based on this basis, the correlation between structure and chiral recognization can be established. The second research was planed to examine the Baylis-Hillman reaction with a new kind of imine catalyst. Imine conpound was rare used as a nucleophilic reagent to initiate reaction in organic chemistry, but in our work ,we found imine can effectively catalyze Baylis-Hillman reaction . So this project will also promise to eatablish a new imine catalytic system.

)：新型催化剂的设计合成及应用是不对称催化的重要内容。本项目拟以吡咯烷为仲胺官能结构，联萘酚骨架为手性环境，设计合成同时具有C2 轴手性与中心手性的新型3-（2'-吡咯烷基）联萘二酚（简称脯氨酚Py-Binol）骨架，并以手性Py-Binol 为母核，设计合成系列新型的手性二烷基氨基吡啶化合物，探索其作为羧酸核磁手性识别试剂的应用研究，考察其构效关系，以期实现氨基酸底物的手性识别。此外，本项目还将对设计合成的亚胺前体化合物催化的Baylis-Hillman反应进行研究，展开亚胺作为亲核试剂启动催化的反应研究， 亚胺作为亲核催化剂催化反应的例子是比较罕见的, 而我们近期的工作发现亚胺能有效催化磺酰亚胺与丁烯酮反应的顺利进行,因此本项目将对亚胺催化反应体系进行更深入研究。