壹、設計並合成以樟腦為基本架構之對掌輔助劑；貳、對掌α,β-不飽和醯胺與苯乙基胺之非鏡像氮丙啶合成反應

陳鵬旭

指導教授 ： 陳焜銘

國立臺灣師範大學/理學院/化學系/碩士(2001年)

摘要

本論文探討以對掌輔助劑控制立體化學中心的建立，利用以樟腦架構為主的對掌輔助劑衍生之對掌醯胺，進行非鏡像的氮丙啶合成反應，生成具有非鏡像選擇性的氮丙啶。對掌輔助劑的製備以 (S)-樟腦酮菘酸 (ketopinic acid) 為起始物，經三步合成步驟所得，總產率在 74% 以上，對掌輔助劑的分子結構由 1H 與 13C NMR 圖譜鑑定，其絕對立體化學結構由 X-ray 單晶繞射解析確定。所衍生的α,β-不飽和醯胺先以過溴化溴口比啶及三乙基胺進行溴化取代，再與苯乙基胺反應，得到所需之氮丙啶的非鏡像超越值達 60% de，產物之立體化學結構由 X-ray 單晶繞射確定。

關鍵字

樟腦 ； 對掌 ； 氮丙啶

並列摘要

Camphor-derived chiral auxiliary camphor pyrazolidinone were prepared and used for asymmetric aziridination. Camphor pyrazolidinone was prepared from the known (S)-ketopinic acid in 3 steps in a total of 74% yield. The structure and absolute stereochemistry of the chiral auxiliary was assigned unambiguously by 1H, 13C NMR spectrum and X-ray crystallographic analysis. The derived N-enoyl pyrazolidinone was reacted with pyridinium hydrobromide perbromide and triethyl amine, then reacted with benzyl amine to obtain desired aziridine in 60% de.

並列關鍵字

camphor ； chiral ； aziridine

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