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(R)-(+)-Binol-Functionalized Mesoporous Organosilica as a Highly Efficient Pre-Chiral Catalyst for Asymmetric Catalysis
Liu, Xiao1,2; Wang, Peiyuan1; Yang, Yan1,2; Wang, Peng1,2; Yang, Qihua1
KeywordAsymmetric Catalysis Chirality Heterogeneous Catalysis Mesoporous Materials Solvent Effects
Source PublicationCHEMISTRY-AN ASIAN JOURNAL
2010
DOI10.1002/asia.200900737
Volume5Issue:5Pages:1232-1239
Indexed BySCI
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
WOS SubjectChemistry, Multidisciplinary
WOS Research AreaChemistry
WOS KeywordSCHIFF-BASE COMPLEX ; ORGANIC-SYNTHESIS ; SILICAS ; FRAMEWORK ; DIETHYLZINC ; ALDEHYDES ; PMOS ; TRANS-(1R,2R)-DIAMINOCYCLOHEXANE ; HYDROGENATION ; SULFOXIDATION
Abstract(R)-(+)-Binol-functionalized chiral periodic mesoporous organosilicas (PMOs) with different framework compositions were successfully synthesized by cocondensation of (R)-2,2'-di(methoxymethyl)oxy-6,6'-di(1-propyl-trimethoxysilyl)-1,1'-binaphthyl (BSBinol) with 1,2-bis(trimethoxysilyl)ethane (BTME) and tetramethoxysilane (TMOS) using triblock copolymer P123 as a template in acidic solution. The mixture of BTME and BSBinol can result in a highly ordered mesostructure in an acidic medium but the mesoporous materials synthesized using a mixture of TMOS and BSBinol can only be obtained in a weak acidic buffer solution. All the materials are efficient catalysts (coordinated with Ti) for asymmetric addition of diethylzinc to aldehydes. The chiral PMO with ethane and (R)-(+)-Binol in the framework exhibits an enantioselectivity as high as 90% with a turnover frequency (TOF) of 104 h(-1), which is even higher than the homogeneous (R)-(+)-Binol catalyst (83% ee with TOF of 96 h(-1)) using toluene as solvent under similar conditions. This work demonstrates the positive effect of the rigid pore wall in increasing the enantioselectivity of the chiral PMOs.
Language英语
WOS IDWOS:000277724800027
Citation statistics
Cited Times:42[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/141668
Collection中国科学院大连化学物理研究所
Affiliation1.Chinese Acad Sci Inst, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China
2.Chinese Acad Sci, Grad Sch, Beijing 100049, Peoples R China
Recommended Citation
GB/T 7714
Liu, Xiao,Wang, Peiyuan,Yang, Yan,et al. (R)-(+)-Binol-Functionalized Mesoporous Organosilica as a Highly Efficient Pre-Chiral Catalyst for Asymmetric Catalysis[J]. CHEMISTRY-AN ASIAN JOURNAL,2010,5(5):1232-1239.
APA Liu, Xiao,Wang, Peiyuan,Yang, Yan,Wang, Peng,&Yang, Qihua.(2010).(R)-(+)-Binol-Functionalized Mesoporous Organosilica as a Highly Efficient Pre-Chiral Catalyst for Asymmetric Catalysis.CHEMISTRY-AN ASIAN JOURNAL,5(5),1232-1239.
MLA Liu, Xiao,et al."(R)-(+)-Binol-Functionalized Mesoporous Organosilica as a Highly Efficient Pre-Chiral Catalyst for Asymmetric Catalysis".CHEMISTRY-AN ASIAN JOURNAL 5.5(2010):1232-1239.
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