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Zinc-prolinamide complex catalyzed direct asymmetric aldol reactions in the presence of water

Science China Chemistry 2010年第11期53卷 2291-2296页

作者： LU ZhiJin MEI HaiBo ZHANG GuangQian HAN JianLin PAN Yi School of Chemistry and Chemical Engineering Nanjing UniversityNanjing 210093China State Key Laboratory of Coordination Chemistry Nanjing UniversityNanjing 210093China

An efficient direct asymmetric aldol reaction with zinc triflate and prolinamides as combined catalysts is reported.A series of chiral prolinamides have been designed and used in the direct aldol reaction resulting in the desired products with excellent yields(up to 94% yield) and high enantioselectivities(up to 96% ee).Water was found to play a significant role in the formation of the aldol products,which suggests a new strategy in the design of new organic catalysts.

关键词： prolinamide Lewis acid aqueous media aldol reaction zinc

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Role of Adamantane Amide Based on L-Proline Double-H Potential Organocatalyst in Aidol Reaction with Product Separated via Host-guest Interaction

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Chemical Research in Chinese Universities 2018年第2期34卷 180-185页

作者： WANG Rui WEI Zhonglin GUO Jing FENG Yusha XU Enjie DUAN Haifeng LIN Yingjie YANG Qingbiao DU Jianshi LI Yaoxian College of Chemistry Jilin University Changehun 130012 P. R. China China-Japan Union Hospital of Jilin University Changchun 130031 P. R. China

Chiral organoeatalysts of 4-adamantane amide based on L-proline with double hydrogen potential were synthesized and used in asymmetric aldol reactions. The reactions were evaluated in toluene under -20℃. A series of aldol products was obtained from moderate to good yields（up to 98%） with excellent diastereoselectivities（up to 〉99：1） and enantioselectivities（up to 〉99%）. The aldol products m the system were separated by a-cyclodextrin via host-guest interaction and determined by chiral HPLC. The catalyst could be reused up to five times. The 4-substitution position played an important role in diastereoselectivitv and enantioselectivitv.

关键词： prolinamide Double hydrogen Aldol reaction Recycle Cyclodextrin

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Stereoselective Aldol Reaction in Aqueous Solution Using Prolinamido-Glycosides as Water-Compatible Organocatalyst

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Modern Research in Catalysis 2015年第1期4卷 20-27页

作者： Daisuke Miura Tomoya Machinami Department of Chemistry College of Science and Technology Meisei University Hino Tokyo Japan

Prolinamido-glycoside catalyzed asymmetric aldol reaction in aqueous media is reported. The reactions are rapid and highly stereoselective when water is used as solvent. The stereoselectivities were under influence of configurations of a prolyl residue of the catalyst and α-chiral aldehydes. Water soluble prolinamido-glycoside catalysts are easily separable from reaction mixture and can be recycled and re-used several times.

关键词： Organocatalyst Aldol Reaction Carbohydrate Water-Compatible prolinamide

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