以手性亞碸催化劑進行醛的不對稱乙基化反應之研究;Enantioselective Ethylation of Aldehydes with Diethylzinc Catalyzed by Chiral Sulfoxide

Please use this identifier to cite or link to this item: http://ir.lib.ncu.edu.tw/handle/987654321/69248

Title:	以手性亞碸催化劑進行醛的不對稱乙基化反應之研究;Enantioselective Ethylation of Aldehydes with Diethylzinc Catalyzed by Chiral Sulfoxide
Authors:	陳致誠;Chen,Chih-Cheng
Contributors:	化學學系
Keywords:	亞碸;不對稱催化;二乙基鋅;乙基化;sulfoxide;asymmetric catalysis;diethylzinc;ethylation
Date:	2015-11-25
Issue Date:	2016-01-05 17:22:18 (UTC+8)
Publisher:	國立中央大學
Abstract:	手性亞碸cis-2及trans-2可以透過市售的5-溴基戊酸乙酯為起始物，經過五步驟合成得到。我們應用這些手性亞碸催化劑進行二乙基鋅不對稱加成到苯甲醛反應上。我們也探討了酸添加劑在這個反應中如何促進催化過程。令人驚訝的是，當我們加入50 mol%的4-甲氧基苯甲酸(4-methoxybenzoic acid)時，發現產率和鏡像選擇性有明顯地改善。而且產物的絕對立體化學形式從S變成R。最後，我們也探討不同的芳香族醛進行二乙基鋅不對稱加成反應。 ;Chiral sulfoxide cis-2 and trans-2 were synthesized from commercially available 5-bromovalerate through a five-step synthetic route. We demonstrated the application of these chiral sulfoxide catalysts in asymmetric addition of diethylzinc to benzaldehyde and also investigated the promotion of the catalytic process by acid additives. Surprisingly, when we added 50 mol% of 4-methoxybenzoic acid, the yield and enantioselectivity were improved. In addition, the stereochemistry of product changed from S to R, Finally, We also investigated asymmetric addition of diethylzinc to different aromatic aldehydes.
Appears in Collections:	[Graduate Institute of Chemistry] Electronic Thesis & Dissertation

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