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Synthesis, characterization and catalytic properties of chiral BINOL functionalized mesoporous silicas for enantioselective Morita-Baylis-Hillman reaction
Wang, Xiaomei1,2; Han, Peng1,2; Qiu, Xuepeng2; Ji, Xiangling1; Gao, Lianxun1,2
2008-08-01
Source PublicationCATALYSIS LETTERS
ISSN1011-372X
Volume124Issue:3-4Pages:418-427
AbstractSeveral Chiral BINOL functionalized mesoporous silicas were prepared by post grafting of organosilane derivatives of (S)-BINOL (1,1'-bi-2-naphthol) on SBA-15 and characterized by (13)C CP/MAS NMR, FT-IR, UV-visible absorption spectra, elemental analysis, powder XRD, nitrogen adsorption-desorption isotherms and TEM techniques. Their catalytic properties were demonstrated in enantioselective Morita-Baylis-Hillman reaction of 3-phenylpropanal and cyclohexenone. Among them, 3BSBA-15 linked through the 3 position of BINOL exhibit higher enantioselectivity (26% e.e.) and yield (88%) which are similar to the homogeneous catalyst (S)-BINOL (27% e.e. and 92% yield) as Bronsted acids catalyst, while complex of 3BSBA-15 and calcium 3BSBA-15-Ca show lower enantioselectivity (21% e.e.) than its homogeneous complex (S)-BINOL-Ca (32% e.e.) as ligand catalyst. 3BSBA-15 and 3BSBA-15-Ca can be reused with no significant decrease in enantioselectivity and yield.
KeywordChiral Organosilane Derivatives Binol Sba-15 As Support Chiral Bronsted Acids Enantioselective Morita-baylis-hillman Reaction
DOI10.1007/s10562-008-9495-4
Indexed BySCI
Language英语
WOS IDWOS:000258528000039
PublisherSPRINGER
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Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/63598
Collection中国科学院化学研究所
Corresponding AuthorJi, Xiangling
Affiliation1.Chinese Acad Sci, State Key Lab Polymer Phys & Chem, Grad Sch, Changchun 130022, Peoples R China
2.Chinese Acad Sci, Lab Polymer Engn, Grad Sch, Changchun Inst Appl Chem, Changchun 130022, Peoples R China
Recommended Citation
GB/T 7714
Wang, Xiaomei,Han, Peng,Qiu, Xuepeng,et al. Synthesis, characterization and catalytic properties of chiral BINOL functionalized mesoporous silicas for enantioselective Morita-Baylis-Hillman reaction[J]. CATALYSIS LETTERS,2008,124(3-4):418-427.
APA Wang, Xiaomei,Han, Peng,Qiu, Xuepeng,Ji, Xiangling,&Gao, Lianxun.(2008).Synthesis, characterization and catalytic properties of chiral BINOL functionalized mesoporous silicas for enantioselective Morita-Baylis-Hillman reaction.CATALYSIS LETTERS,124(3-4),418-427.
MLA Wang, Xiaomei,et al."Synthesis, characterization and catalytic properties of chiral BINOL functionalized mesoporous silicas for enantioselective Morita-Baylis-Hillman reaction".CATALYSIS LETTERS 124.3-4(2008):418-427.
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