葉名倉Yeh, Ming-Chang胡婷嘉Hu, Ting-Chia2019-09-04不公開2019-09-042015http://etds.lib.ntnu.edu.tw/cgi-bin/gs32/gsweb.cgi?o=dstdcdr&s=id=%22G060242038S%22.&%22.id.&http://rportal.lib.ntnu.edu.tw:80/handle/20.500.12235/99972本文分別探討以金、銀與三氯化鐵共輔佐及單獨以三氯化鐵作為路易士酸輔佐4-炔醯胺環己-2-烯醇衍生物進行分子內環化反應。第一部分探討以三氯化鐵輔佐4-炔醯胺-1-矽氧基環己-2-烯醇衍生物，在室溫及氮氣下進行Friedel-Craft反應合成氯化二苯氮呯衍生物。以金、4-炔醯胺-1-矽氧基環己-2-烯醇衍生物銀與三氯化鐵共輔佐4-炔醯胺-1-矽氧基環己-2-烯醇衍生物在室溫及氮氣下生成keteniminium和金碳烯中間體後，進行碳-鹵化反應得到六氫吲哚酮衍生物。第二部分探討4-炔醯胺-1-乙醯氧基環己-2-烯在三氯化鐵輔佐及金、銀與三氯化鐵共催化下，生成keteniminium和碳烯中間體後，進行反式碳－鹵化反應得到六氫吲哚酮衍生物。This thesis focuses on gold(I)/silver/iron trichloride-copromoted and iron trichloride-promoted intramolecular cyclolization of cyclic 2-enynamides. First, iron trichloride promoted intramolecular cyclization of 1-siloxy-4-ynamidocyclohex-2-enes under nitrogen at room temperature proceeded via Friedel-Craft reaction to produced benzazeprine derivatives. Gold(I)/iron trichloride-copromoted 1-siloxy-4-ynamidocyclohex-2-enes under nitrogen at room temperature afforded oxindole derivatives with good stereoselectivity. The carbohalogenation was suggested via formation of the transient keteniminium ion and gold-carbene intermediates. Second, gold(I)/iron trichloride-copromoted cyclization of 1-acetoxy-4-ynamidocyclohex-2-enes under nitrogen at room temperature generated hexahydroxindole derivatives via carbohalogenation.三氯化鐵炔醯胺化合物分子內環化氯化二苯氮呯衍生物金銀與三氯化鐵共輔佐碳-鹵化反應六氫吲哚酮衍生物iron trichlorideenynamidesintramolecular cyclolizationbenzazeprinegold(I)/silver/iron trichloride-copromotedcarbohalogenationhexahydroxindole