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Chirally Functionalized Hollow Nanospheres Containing L-Prolinamide: Synthesis and Asymmetric Catalysis
Gao, Jinsuo; Liu, Jian; Tang, Jianting; Jiang, Dongmei; Li, Bo; Yang, Qihua; Yang QH(杨启华)
KeywordAldol Reaction Heterogeneous Catalysis Nanostructures Organocatalysis Prolinamide
Source PublicationCHEMISTRY-A EUROPEAN JOURNAL
2010
DOI10.1002/chem.201000161
Volume16Issue:26Pages:7852-7858
Indexed BySCI
SubtypeArticle
Department5
Funding Project506
Contribution Rank1;1
WOS HeadingsScience & Technology ; Physical Sciences
WOS SubjectChemistry, Multidisciplinary
WOS Research AreaChemistry
WOS KeywordPERIODIC MESOPOROUS ORGANOSILICA ; SULFONIC-ACID FUNCTIONALIZATION ; DIRECT ALDOL REACTIONS ; STEREOSELECTIVE CATALYSTS ; RECYCLABLE ORGANOCATALYST ; MCM-41-TYPE SILICA ; COMBINED ALKYL ; SPHERES ; WATER ; POLYSTYRENE
AbstractChirally functionalized hollow nanospheres with different surface properties were successfully synthesized by co-condensation of (2S,1'R,2'R)-N-tert-butyloxycarbonylpyrrolidine-2-carboxylic acid [2'-(4-trimethoxysilylbenzylamide)cyclohexyl] amide with 1,2-bis(trimethoxysilyl)ethane or tetramethoxysilane using F127 (EO(106)PO(70)EO(106)) as surfactant in water. The TEM and N(2) sorption characterizations show that the particle size of the hollow nanosphere is 15-21 nm with a core diameter of 10-16 nm. These L-prolinamide-functionalized hollow nanospheres are highly efficient solid catalysts for the direct asymmetric aldol reaction between cyclohexanone and aromatic aldehydes. It was found that the addition of water in the reaction system not only enhanced the catalytic activity but also increased the enantioselectivity, which is probably due to the enhanced hydrogen bond between the amide oxygen atom and the hydroxyl group of water. Moreover, the catalytic activity increases sharply as the surface hydrophobicity of the hollow nanospheres increases. These hollow nanospheres are quite stable and can be reused with almost the same enantioselectivity and only a slight decrease in catalytic activity.
Language英语
URL查看原文
WOS IDWOS:000280431900026
Citation statistics
Cited Times:36[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/103183
Collection中国科学院大连化学物理研究所
Corresponding AuthorYang QH(杨启华)
AffiliationChinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China
Recommended Citation
GB/T 7714
Gao, Jinsuo,Liu, Jian,Tang, Jianting,et al. Chirally Functionalized Hollow Nanospheres Containing L-Prolinamide: Synthesis and Asymmetric Catalysis[J]. CHEMISTRY-A EUROPEAN JOURNAL,2010,16(26):7852-7858.
APA Gao, Jinsuo.,Liu, Jian.,Tang, Jianting.,Jiang, Dongmei.,Li, Bo.,...&杨启华.(2010).Chirally Functionalized Hollow Nanospheres Containing L-Prolinamide: Synthesis and Asymmetric Catalysis.CHEMISTRY-A EUROPEAN JOURNAL,16(26),7852-7858.
MLA Gao, Jinsuo,et al."Chirally Functionalized Hollow Nanospheres Containing L-Prolinamide: Synthesis and Asymmetric Catalysis".CHEMISTRY-A EUROPEAN JOURNAL 16.26(2010):7852-7858.
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