對掌輔助劑衍生物之非對稱氮丙啶合成探討

段蓓文(Tuan Pei-Wen)

指導教授 ： 陳焜銘

國立臺灣師範大學/理學院/化學系/碩士(2002年)

摘要

無資料

關鍵字

氮丙啶 ； 對掌輔助劑 ； 樟腦

並列摘要

Aziridine is an important building block found in many nature products. The preparation of enantiomerically pure compounds is one of the major areas in organic chemistry. The synthesis of aziridines and their derivaties has attracted a lot of attention in recent years, owing to their versatile roles in organic synthesis.
A new chiral auxiliary was prepared to react with acyl chloride（302）, and get α,β-unsaturated carbonyl substrates（291-301）of exo-10,10-diphenyl-2,10- camphanediol（288）. The formation of aziridines was carried out by reactions of various chiral auxiliary derivatiesα,β-unsaturated olefins with N-aminophthalimide in the presence of lead tetracetate. These reactions was performed in tetrahydrofuran（THF）at 0 ℃ for 5-15 min, and the products were obtained in good yield（80-95%） and good diastereoselectivity（>90% de）. All structures are determined by 1H NMR, 13C NMR, HRMS, element analysis, and X-ray ORTEP.
The effects of solvent, temperature, and different substrates of chiral olefins were investigated, THF was found to be the best choice of solvent because of the reactivity. The more hindered the substrate is, the higher diastereoselectivity is generated.
The chiral auxiliary was removed by using sodium methoxide in methanol at room temperature with a recovered yield 85%.

並列關鍵字

aziridine ； chiral ； camphor

參考文獻

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