本論文主要研究樟腦衍生之掌性催化劑催化不對稱碳-碳鍵生成反應之研究。論文共分為三部分，第一部份在探討()-MINBOL 8與Ni(acac)2形成的掌性錯合物催化不對稱串聯麥可/麥可加成反應，可成功地得到66–84%的加成產物，非鏡像選擇性為>20:1，鏡像選擇性為91–97% ee。第二部份旨在將具有樟腦骨架之有機催化劑應用至催化醛類與炔基醛進行不對稱羥醛反應(aldol reaction)，建立具光學活性的丙炔基醇。以5 mol%催化劑58進行催化反應時，得到anti位向為主產物，產率最高可達95%，鏡像選擇性anti : 91–99% ee; syn : 86–98% ee; 而以5 mol%之催化劑66進行催化反應時，得到syn位向為主產物，產率最高可達93%，鏡像選擇性anti : 82–90% ee; syn : 97–99.5% ee。第三部份則是設計且成功合成新型掌性三氮唑鹽97並應用至催化苯甲醛進行不對稱安息香縮合反應，可得到90%之產物以及67%的鏡像超越值。

This thesis reported the application of camphor-derived chiral catalysts in the asymmetric carbon-carbon bond forming reactions. In the first section, we demonstrated the in situ generated chiral complex from 12.5 mol% of (+)-MINBOL 8 and 0.5 mol% of Ni(acac)2 successfully catalyzed asymmetric tandem double Michael reactions. The tandem adducts were produced in high yields (66–84%) with excellent diastereoselectivities (>20:1) and high enantioselectivities (91–97% ee).The second section described the synthesis of the chiral propargylic alcohol by the cross-aldol reaction with alkynals catalyzed by camphor-derived organocatalysts. The reactions in the presence of 5 mol% catalyst 58 resulted in good yields (up to 95%) with moderate diastereoselectivities (anti:syn = 55:45–75:25) and high enantioselectivities (anti : 91–99% ee; syn : 86–98% ee). On the other hand, the reactions in the presence of 5 mol% catalyst 66 resulted in good yields (up to 93%) with good diastereoselectivities (anti:syn = 25:75–10:90) and high enantioselectivities (anti : 82–90% ee; syn : 97–99.5% ee).The final section focused on the design of novel chiral triazolium salt 97 and its application in the asymmetric benzoin condensation. The product was furnished in 90% yield with moderate enantioselectivity (67% ee).

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