一、以酮類分子為起始物進行一鍋化合成醯醇類分子之研究
二、以掌性甲基[ 3.2.1 ]雙環胺醇化合物為有機催化劑進行不對稱加成反應

第一部分：本實驗室之前合成醯醇類分子是經由三個步驟1，首先進行witig反應形成phenylmethylene alkene，phenylmethylene alkene再與OsO4及T.M.O.氧化形成雙醇化合物，之後將二級醇氧化形成醯醇類分子。經由三步驟的合成的總產率不佳。因此本實驗想利用1,3-dithiane為試劑進行一鍋化合成反應。因此，於一鍋化合成反應下，首先利用正丁基鋰及2-phenyl-1,3-dithiane於低溫下反應，再將茚酮類分子加入，形成中間體1,3-dithiane衍生物，然後使用NBS-AgNO3試劑將dithiane水解獲得各種1-acyl-1-indanols。因此，我們其實驗方法使用於其他酮類分子，且成功得到目標產物。此製備1-acyl-1-indanols較實驗室之前實驗路徑簡略且我們成功利用一鍋化反應經由中間體1,3-dithiane衍生物轉換形成不同的醯醇類化合物。第二部分：不對稱Michael加成反應及Friedel-Crafts烷基化反應是碳-碳形成最有影響力的反應，且其研究為有機化學發展中的重要角色。於本實驗是研究中，以樟腦及L-proline為起始物合成新型的pyrrolidine衍生物194為催化劑。以不同取代基醛類和硝基烯烃類為起始物進行不對稱Michael加成反應，測試是否有良好的產率與立體選擇性。亦將催化劑194運用於不對稱Friedel-Crafts烷基化反應，以indole和硝基苯乙烯為起始物，測試是否有良好的產率與立體選擇性。雖然不對稱Michael加成反應及 Friedel-Crafts烷基化反應沒有較好的產率及良好的立體選擇性，本實驗室希望催化劑194未來可以運用於不同的催化反應。

關鍵字

一鍋化反應； 1-茚酮類分子； dithiane 衍生物；樟腦；不對稱Michael反應； Friedel-Crafts烷基化反應

並列摘要

Ⅰ、In our laboratory, we had synthesized of 1-acyl-1-indanols via three steps1, before. First, a wittig reaction of indanone molecules with benzyltriphenyl-phosphoniumchloride, in the presence of butyl lithium, furnished phenylmethyl alkene. Then, dihydroxylation of phenylmethyl alkene with Osmium tetraoxide and T.M.O. reaction gave a diol compound, in which the secondary group was further oxidized to carbonyl. Poor overall yield via three steps. Therefore, we use 1,3-dithiane as areagent for one-pot synthesis. Thus, in a one-pot synthesis reaction. First, at low temperature of n-BuLi and 2-phenyl-1,3-dithiane, and added the indanone molecular form intermediate 1,3-dithiane derivative, and then hydrolysis by NBS-AgNO3 form 1-acyl-1-indanols. Therefore, this method use in other ketone molecules, and we successfully to the the target compounds. This method is simple more than before, and we successful use of one-pot synthesis reaction via intermediate 1,3-dithiane derivatives converted form acyl alcohol derivatives. Ⅱ、The Michael addition reaction and Friedel-Crafts are generally regarded as one of the most efficient carbon-carbon bond forming reactions, and studies concerning this reaction have play an important role in the development of organic chemistry. In this study, a new class of pyrrolidine derivative 194 prepared from camphor and L-proline. The direct Michael addition reaction of variety aldehyde to nitrostyrene, and using nitrostyrene as substrates to achieve asymmetric Friedel-Crafts alkylation of indole has been paid considerable attention. Although they can’t get good result in Michael addition reaction and Friedel-Crafts reaction, we hope the organocatalyst 194 can catalyze other reactions with high chemical tield and diastereo- and enantioselectivity in the future.