以手性有機硫催化劑進行不對稱環丙烷化反應並應用於合成?咯類化合物之研究;(Thiolan-2-yl)diphenylmethanol Benzyl Ether-catalyzed Asymmetric Cyclopropanation and Its Application to the Synthesis of Pyrrole Derivatives

Please use this identifier to cite or link to this item: http://ir.lib.ncu.edu.tw/handle/987654321/84890

Title:	以手性有機硫催化劑進行不對稱環丙烷化反應並應用於合成?咯類化合物之研究;(Thiolan-2-yl)diphenylmethanol Benzyl Ether-catalyzed Asymmetric Cyclopropanation and Its Application to the Synthesis of Pyrrole Derivatives
Authors:	包慧彥;Pao, Hui-Yen
Contributors:	化學學系
Keywords:	不對稱環丙烷化反應;合成?咯類化合物;手性有機硫催化劑;Asymmetric Cyclopropanation;Synthesis of Pyrrole Derivatives;chiral sulfur catalyst
Date:	2021-01-13
Issue Date:	2021-03-18 16:45:51 (UTC+8)
Publisher:	國立中央大學
Abstract:	在天然物與藥物中經常出現五員環結構，因此[4+1]環化反應受到了重視。在[4+1]環化反應中，起始物大多為,-不飽和化合物，而硫偶極體(sulfur ylide)與,-不飽和化合物大多進行[2+1]環化反應，故想要利用硫偶極體進行反應，得到五員環產物是有很大的挑戰性。本研究主要目標為利用實驗室開發的手性硫化物(S)-1作為不對稱環丙烷化反應催化劑，合成三員環化合物，再添加路易士酸進行擴環反應得到五員環?咯類產物。起始物使用1-氮雜二烯(1-azadienes)，透過2-羥基苯乙酮經過四步驟合成得到。我們也探討反應如何獲得良好的鏡像超越值。 ;Five-membered ring is an important structure in natural product and medicinal chemistry, and therefore [4+1] annulation has attracted much attention from organic chemists. While most of the [4+1] annulations were based on ,-unsaturated starting materials, using sulfur ylides and ,-unsaturated compounds to construct five-membered rings still remains a challenge. The main goal of this thesis is to use sulfur catalyst (S)-1 for developing asymmetric cyclopropanations of 1-azadienes. The resulting cyclopropanes were the treated with Lewis acid for ring-expansion to give five-membered rings. The starting material, 1-azadienes, was synthesized through a 4-step process from 1-(2-hydroxyphenyl)ethan-1-one.
Appears in Collections:	[Graduate Institute of Chemistry] Electronic Thesis & Dissertation

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