在本篇論文中我們成功地利用鈷金屬催化系統來完成亞胺與不飽和碳－碳鍵的[3+2]環化反應來合成飽和與不飽和茚胺的衍生物，此合成方法可以快速地建立具有取代的茚胺骨架，對於相關的天然物或是藥物的衍生物提供了一個非常有力的合成方法。在第二章中我們利用鈷金屬錯合物來催化鄰位具有亞胺的苯硼酸與共軛烯類的[3+2]環化反應，可以得到具有酯基的飽和茚胺衍生物且反應具有非常高的化學反應性及立體選擇性。而在第三章的部份我們延續了第二章的基礎，利用鈷金屬錯合物來催化鄰亞胺苯硼酸與炔類的[3+2]環化反應來合成不飽和茚胺化合物，同時我們也使用了藉由胺基酸製備出的掌性配位基加入催化反應，並得到具有很好的位向及鏡像選擇性的不飽和茚胺衍生物，而藉由一步催化反應來得到具有掌性中心的茚胺衍生物在文獻中是非常稀少的。最後在第四章中我們根據之前實驗室發表的鈷金屬催化鄰亞胺碘化苯與炔類的[3+2]環化反應為基礎，進一步改良反應並使用前一章所製備的掌性配位基搭配鈷金屬共同催化鄰亞胺溴化苯與炔類的[3+2]環化反應來得到具有掌性中心的不飽和茚胺化合物，在反應中我們合成出具有多取代的茚胺衍生物，且我們也發現反應具有不錯的位向及優異的鏡像選擇性。藉由絕對結構的鑑定我們可以更清楚地知道反應過程中鈷金屬錯合物可能的環境結構。

In this thesis, we successfully develop cobalt-catalyzed [3+2] annulation reactions of imine with unsaturated bonds and synthesize aminoindane-and indenes derivatives with efficiency. By these methodologies, we can construct aminoindane or indene skeletons in one step and it is also powerful synthetic methods for the synthesis of relative aminoindane or indene natural product and drugs.
In chapter 2, we develop cobalt-catalyzed [3+2] annulation of 2-iminoarylboronic acids with conjugate alkenes to synthesize aminoindane carboxylate derivatives with high chemo-and diastereoselectivity.
In chapter 3, we extend the result of chapter 2 and synthesize aminoindene derivatives by cobalt-catalyzed [3+2] annulation of 2-iminoarylboronic acids with alkynes. Furthermore, we combine PHOX chiral ligands which are prepared from commercial available amino acids in the cobalt catalysis reaction and generate a series of chiral aminoindenes with high regio-and enantioselectivity.
In the final chapter, based on our cobalt catalysis system of aryl halides with other substrates experience before, we develop cobalt-catalyzed asymmetric [3+2] annulation of 2-iminoarylbromides with alkynes to construct chiral aminoindenes. In this reaction, we can prepare multi-substituted chiral aminoindenes with good to excellent regio-and enantioselectivity. Besides, we can learn more about the relative position of chiral cobalt complex and substrates in the reaction environment via absolute configuration determination.

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