酸催化噁唑烷酮稠合吖環丙烷進行開環反應之合成研究

Please use this identifier to cite or link to this item: http://ir.lib.ncu.edu.tw/handle/987654321/94700

Title:	酸催化噁唑烷酮稠合吖環丙烷進行開環反應之合成研究
Authors:	蔡宗倫;Tsai, Tsung-Lun
Contributors:	化學學系
Keywords:	唑烷酮稠合吖環丙烷;酸催化開環;KRN7000;Oxazolidinone Fused Aziridines;acid-catalyzed ring-opening
Date:	2024-08-14
Issue Date:	2024-10-09 15:24:52 (UTC+8)
Publisher:	國立中央大學
Abstract:	第一部分: KRN7000 肌醇類似物之合成研究以 1,4-戊二烯-3-醇為起始物，利用夏普萊斯不對稱環氧化反應 (Sharpless epoxidation) 生成兩個立體中心，接著以高效率微波加熱的方式進行立體選擇性分子內吖環丙烷化 (stereoselective intramolecular aziridination) 以具有非鏡像選擇性的反應建立第三個立體中心，而最關鍵的步驟則是利用肌醇衍生物對吖環丙烷進行開環反應生成碳-氧鍵，最後經數步反應即可獲得具有五種不同長度醯基鏈的 KRN7000 肌醇類似物。第二部分: 酸催化醇對噁唑烷酮稠合吖環丙烷進行開環反應對單至三取代的噁唑烷酮稠合吖環丙烷以一至三級醇，進行酸催化開環反應的研究。此方法大幅縮短了反應時間，並且在室溫下就能進行反應，得到有立體選擇性的單一非鏡像的化合物。 ;Part 1. Research on the Synthesis of KRN7000 Inositol Analogs Using 1,4-pentadiene-3-ol as the starting material and utilizing Sharpless asymmetric epoxidation, two stereocenters were generated selectively. Subsequently, stereoselective intramolecular aziridination was carried out with high efficiency using microwave heating to establish the third stereocenter with high diastereoselectivity. The ring-opening of the aziridine by inositol derivatives to form a carbon-oxygen bond was critical. Further chemical transformations, five target KRN7000 inositol analogs with different lengths of acyl chains were obtained. Part 2. Acid-Catalyzed Ring-Opening of Oxazolidinone Fused Aziridines by Alcohols This study investigated acid-catalyzed ring-opening reactions of mono-, di and tri-substituted oxazolidinone-fused aziridines with primary, secondary and tertiary alcohols. This method significantly shortened the reaction time and allowed the reaction acurred at room temperature to yield the products with high stereoselectivity.
Appears in Collections:	[Graduate Institute of Chemistry] Electronic Thesis & Dissertation

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