CAJ | 학술논문

目的：研究α，β不饱和酮的不对称环氧化反应。方法：利用手性的3-取代联二萘酚和Fe3+、La3+、Al3+的配和物诱导不对称环氧化反应。结果：成功合成了三个3取代联二萘酚衍生物，并将其运用于不对称环氧化反应。手性La3+配合物催化的环氧化反应，取得88%的产率以及46%对映异构体过量；手性Fe3+和Al3+配合物体系，环氧化产率较高，产物为消旋体。结论：手性的3-羟甲基联二萘酚镧配合物能够催化α，β不饱和酮的不对称环氧化反应并获得较高产率和中等的对映选择性。对该不对称环氧化反应的研究，为合成光活性环氧化物类药物中间体提供了新方法。
목적：연구α，β불포화동적불대칭배양화반응。방법：이용수성적3-취대련이내분화Fe3+、La3+、Al3+적배화물유도불대칭배양화반응。결과：성공합성료삼개3취대련이내분연생물，병장기운용우불대칭배양화반응。수성La3+배합물최화적배양화반응，취득88%적산솔이급46%대영이구체과량；수성Fe3+화Al3+배합물체계，배양화산솔교고，산물위소선체。결론：수성적3-간갑기련이내분란배합물능구최화α，β불포화동적불대칭배양화반응병획득교고산솔화중등적대영선택성。대해불대칭배양화반응적연구，위합성광활성배양화물류약물중간체제공료신방법。
Objective: To study the asymmetric epoxidation of α,β-unsaturated ketone with BINOL derivative as catalyst. Method: The chiral 3-substitued-BINOL derivative ligands were first synthesized ,and then coordinated with Fe3+, La3+or Al3+to catalyze the asymmetric epoxidation of chalcone. Results: The 3-substituted BINOL derivatives (4~5) were successfully synthesized and applied in the asymmetric epoxidation of chalcone. The optical active epoxide was obtained in high yield (88%) and moderate ee value (46%) with 3-hydroxyl-methylnaphthol/La3+ as catalyst,while poor enantioselectivity was observed when the 3-hydroxylmethylnaphthol/Fe3+or 3-hydroxylmethylnaphthol/Al3+complex was used. Conclusion: The chiral 3-hydroxylmethylnaphthol/La3+complex is able to catalyze the asymmetric epoxidation of chalcone in high yield and moderate enantioselectivity , which pvovides a new approach to the construction of optical epoxide intermediate in the synthesis of material and medicine.