本篇論文分為四個章節探討以金催化劑與鋅催化劑進行新穎的有機合成反應，其中包含了氧化環化反應、高立體選擇性[2+2+3]環化反應、1,4-雙羰基化合物合成與1,4-復分解反應等。
第一部分利用金催化劑催化1,5烯炔化合物並與氧化劑(8-Methylquinoline N-Oxide)進行氧化環化反應而得茚酮類化合物。天然物中常會見到茚酮化合物的骨架存在，而此骨架的合成是經由氧化炔類而得的α-羰基中間體再度進行碳環化而成。

第二章結講述的為金催化劑催化1,6烯炔類化合物與硝酮進行[2+2+3]環化反應並且得到高度的鏡像與非鏡像選擇性產物。此反應對於1,6烯炔與硝酮化合物的官能機有極大的容忍度，並且此氮氧結構對於接續的應用與生物上的合成皆有極大的用處。

第三章敘述一種新穎的方式在3-烯1-炔類化合物進行1,4-雙羰基化合物的合成。利用一鍋方式可將低活性的3-芳香環-3-烯-1炔化合物反應成1,4-雙羰基化合物，並且有高度的Z- E-選擇性。而其反應機構是經由類呋喃化合物中間體，其氫化間參與了烯類氟化反應而得。本部分是第一個成功將3-烯1-炔類化合物合成至1,4-雙羰基化合物的反應。

第四章則是利用催化劑將3-烯1-炔氮基化合物與芳香亞硝基進行復分解反應，此反應經由銀催化劑與鋅催化劑催化後可得到非預期的3-聯胺基炔類化合物與苯醛，並且進一步的將此兩化合物進行加成而得1,4-氧氮基化合物。

This dissertation describes the development of new synthetic organic transformation by using gold and zinc salts. Transition metal-catalyzed organic transformations such as Oxidative Cyclization, Di-stereo and Enatioselective [2+2+3] cycloaddition, 1,4-Dioxo Functionalizations, 1,4-Metathesis Reactions of appropriately functionalized organic molecules are described in this dissertation. For sake of convenience and better understanding, the thesis is divided into four chapters.
The first chapter deals with the Gold-Catalyzed Oxidative Cyclization of 1,5-Enynes Using External Oxidants (8-Methylquinoline N-Oxide) to deliver indanone frameworks. Such indanone core is one of the most commonly encountering skeletons in nature. The core structure of the resulting products are construct through a formal reactions proceed through prior oxidations of alkyne to form α-carbonyl intermediates, followed by intramolecular carbocyclizations.

The second chapter deals with the Gold-catalyzed diastereo- and enantioselective [2+2+3]-cycloaddition reactions of 1,6-enynes with nitrones. The utility of such reactions is manifested by a wide substrate scopes of 1,6-enynes and nitrones. This Gold-catalyzed diastereo- and enantioselective [2+2+3]-cycloaddition reactions of 1,6-enynes with nitrones deliver 1,2-Oxazepane core which has wide aplication in structural and biological importance.

The third chapter describes new 1,4-oxo functionalizations of 3-en-1-ynes based on a hydrative oxidation approach. The one-pot dioxo reactions were applicable to various 3-en-1-ynes including unactivated 3-aryl-3-en-1-ynes, giving Z- or E-configured 2-en-1,4-dicarbonyl compounds selectively. In this chapter, mechanistic analysis supported an initial formation of furan intermediates, generated from carbonyl-assisted alkenyl fluorinations of hydration intermediates. This work reports the first success for 1,4-oxo functionations of readily available 3-en-1-ynes to offer highly functionalized alkenes.
The fourth chapter presents Catalyst-dependent metathesis reactions between 3-en-1-ynamides and nitrosoarenes are described. Particularly notable are the unprecedented 1,4-metathesis reactions catalyzed by Ag(I) or Zn(II) to give 3-imidoylalkynes and benzaldehyde. With 3-en-1-ynamides bearing a cycloalkenyl group, 1,4-oxoimination products were produced efficiently without molecular fragmentation. We have developed metathesis/alkynation cascades for terminal 3-imidoylalkynes and benzaldehyde species generated in situ, to manifest 1,4-hydroxyimination reactions of 3-en-1-ynes.

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