【摘要】：N-雜環(huán)卡賓作為化學(xué)反應(yīng)的催化劑,在有機(jī)催化反應(yīng)中扮演著重要的角色,它們不僅可以作為親核試劑參與反應(yīng),也可以作為路易斯堿和布朗斯特堿參與有機(jī)催化反應(yīng)。目前,N-雜環(huán)卡賓催化劑仍然是有機(jī)催化反應(yīng)中的研究熱點之一。N-雜環(huán)卡賓催化劑手性骨架的引入,可以很方便地不對稱合成不同骨架的化合物。本論文主要圍繞N-雜環(huán)卡賓催化下δ-內(nèi)酰胺骨架、螺吲哚四氫吡喃-2-酮骨架及萘并二氫吡喃酮骨架的串聯(lián)合成等課題進(jìn)行展開。研究工作包括以下四個部分。第一部分:介紹了N-雜環(huán)卡賓的發(fā)現(xiàn)、結(jié)構(gòu)的確認(rèn)、參與催化反應(yīng)的性質(zhì)和類型,以及近年來N-雜環(huán)卡賓的發(fā)展歷史。最后介紹了該論文的創(chuàng)新點。第二部分:介紹了手性卡賓催化酰腙與α-溴代-α,β-不飽和醛的反應(yīng),不對稱地合成δ-內(nèi)酰胺骨架衍生物。這種方法具有高產(chǎn)率、高對映選擇性、原料易得、反應(yīng)條件溫和等特點。第三部分:介紹N-雜環(huán)卡賓催化溴代烯醛與氧化吲哚非對映選擇性構(gòu)建螺吲哚四氫吡喃-2-酮骨架。這種方法具有原料易得、非對映選擇性高、產(chǎn)率較好等優(yōu)點。進(jìn)一步發(fā)展了螺吲哚四氫吡喃-2-酮的合成途徑。第四部分:介紹N-雜環(huán)卡賓催化溴代烯醛與β-四氫萘滿酮來不對稱構(gòu)建萘并二氫吡喃酮骨架。這種方法具有簡便易得的原料、產(chǎn)率很好和對映選擇性很高等優(yōu)點。
[Abstract]:N- heterocyclic carbene, as a catalyst for chemical reaction, plays an important role in organic catalytic reactions. They can be used not only as nucleophilic reagents, but also as Lewis base and Brownst base to participate in organic catalytic reactions. At present, N-heterocyclic carbene catalyst is still one of the hot spots in organic catalytic reaction. The introduction of chiral skeleton of N-heterocyclic carbene catalyst can facilitate asymmetric synthesis of compounds with different skeletons. This thesis focuses on the series synthesis of 未-lactam framework, spiroindole tetrahydropyrane-2-one skeleton and naphthalene dihydropyranone skeleton catalyzed by N-heterocyclic carbene. The research includes the following four parts. The first part introduces the discovery of N-heterocyclic carbene, the confirmation of structure, the nature and type of catalytic reaction, and the development history of N-heterocyclic carbene in recent years. Finally, the innovation of this paper is introduced. The second part: chiral carbene catalyzed the reaction of acylhydrazone with 偽-bromo- 偽, 尾-unsaturated aldehydes and asymmetric synthesis of 未-lactam skeleton derivatives. This method is characterized by high yield, high enantioselectivity, easy availability of raw materials and mild reaction conditions. Part three: N-heterocyclic carbene catalyzed the enantioselectivity of brominoalkenal and oxindole to construct spiroindole tetrahydropyran-2-one skeleton. This method has the advantages of easy preparation of raw materials, high enantioselectivity and good yield. The synthesis of spiroindole tetrahydropyran-2-one was further developed. Part four: N-heterocyclic carbene catalyzed the asymmetric construction of naphthalene dihydropyranone framework with brominated aldehydes and 尾 -tetrahydronaphthalenone. This method has the advantages of simple and easy to obtain raw materials, good yield and high enantioselectivity.
【學(xué)位授予單位】：江蘇師范大學(xué)
【學(xué)位級別】：碩士
【學(xué)位授予年份】：2017
【分類號】：O621.251

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