在1992年MobilOil公司利用帶正電性四級銨鹽之界面活性劑當模版,與帶負電荷之矽酸鈉結合,成功地開發出一系列孔洞大小介於1.5~10.0 nm層次之氧化矽分子篩。由於此系列中孔洞分子篩具有高表面積、熱穩定性高、孔洞大小一致及可調整大小的孔洞等優點，近年來吸引了許多科學家的興趣與重視。本實驗即利用此系列之一的MCM-41 (Mobil Composite of Matter 41)原有的優勢作為主架構結合不同左旋脯胺基酸衍生物作為非均勻相之有機催化劑。
在中孔洞非均勻相有機催化劑的鑑定方面，以X射線粉末繞射儀(XRD)來鑑定產物之結晶構造，同時為瞭解有機矽源成分是否進入中孔洞分子篩，我們以13C、29Si 固態NMR 探測；而表面積、孔洞分佈之量測則使用氮氣吸附儀；並利用元素分析法推算出中孔洞分子篩內的有機莫耳含量；最後分別以穿透式顯微鏡(TEM)及掃描式電子顯微鏡(SEM)來鑑定產物的結構。
利用中孔洞非均勻相有機催化劑，以對-硝基苯甲醛和環己酮作為反應物，催化不對稱醇醛縮和反應。並有效利用飽和食鹽水作為反應最佳溶劑，可達到大於95%的產率以及合理的非鏡像超越值60 % de 和鏡像超越值40 % ee。亦可利用其非均勻相特性,達到催化劑回收重複使用的效果。亦合成雙官能基中孔洞非均勻相有機催化劑，於相同反應條件進行不對稱aldol反應，在不影響產物鏡像選擇性下有效提升反應性。
如何修飾有機部分使其能在高產率情況下，更有效提高反應的鏡像超越值（% ee）以及非鏡像超越值（% de），將是日後研究的主要重點。

Mesoporous silica functionalized L-proline amide derivative was synthesized by the method of co-condensation with high overall chemical yield. The features of the organic-inorganic hybrid material were fully characterized with low angle X-ray XRD diffraction、SEM、TEM、nitrogen adsorption/desorption (BET, BJH) and solid state of 13C CP- and 29Si DPMAS NMR. We used it as a heterogeneous chiral organocatalyst in asymmetric aldol reaction. Comparable diastereo- and enantiosele-
ctivity were obtained in aldol reaction with the counter homogeneous catalyst when the heterogeneous catalyst was used. We also studied the recycling of the uniformly heterogeneous catalyst and the result indicated that the mesopores of L-proline amide derived material were not destroyed by chemical decomposition during the repeated use as a catalyst. Finally we synthesized bi-funtionalized mesoporous silica nanosphere as new organocatalyst in asymmetric aldol reaction, in order to increase the reactivity by secondary functional group. The development of novel chiral organocatalysts and the incorporation onto the mesoporous materials are in progress and further applications will be reported.

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