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(R)-(+)-Binol-functionalized mesoporous organosilica as a highly efficient pre-chiral catalyst for asymmetric catalysis.
Chem Asian J. 2010 May 03; 5(5):1232-9.CA

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-propyltrimethoxysilyl)-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.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Liu X
State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences Institution, 457 Zhongshan Road, Dalian 116023, China.
Wang P
No affiliation info available
Yang Y
No affiliation info available
Wang P
No affiliation info available
Yang Q
No affiliation info available

MeSH

AldehydesCatalysisEthaneNaphthalenesOrganometallic CompoundsPorositySilanesSilicon DioxideSolventsStereoisomerismTrimethylsilyl Compounds

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

20235277

Citation

Liu, Xiao, et al. "(R)-(+)-Binol-functionalized Mesoporous Organosilica as a Highly Efficient Pre-chiral Catalyst for Asymmetric Catalysis." Chemistry, an Asian Journal, vol. 5, no. 5, 2010, pp. 1232-9.
Liu X, Wang P, Yang Y, et al. (R)-(+)-Binol-functionalized mesoporous organosilica as a highly efficient pre-chiral catalyst for asymmetric catalysis. Chem Asian J. 2010;5(5):1232-9.
Liu, X., Wang, P., Yang, Y., Wang, P., & Yang, Q. (2010). (R)-(+)-Binol-functionalized mesoporous organosilica as a highly efficient pre-chiral catalyst for asymmetric catalysis. Chemistry, an Asian Journal, 5(5), 1232-9. https://doi.org/10.1002/asia.200900737
Liu X, et al. (R)-(+)-Binol-functionalized Mesoporous Organosilica as a Highly Efficient Pre-chiral Catalyst for Asymmetric Catalysis. Chem Asian J. 2010 May 3;5(5):1232-9. PubMed PMID: 20235277.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - (R)-(+)-Binol-functionalized mesoporous organosilica as a highly efficient pre-chiral catalyst for asymmetric catalysis. AU - Liu,Xiao, AU - Wang,Peiyuan, AU - Yang,Yan, AU - Wang,Peng, AU - Yang,Qihua, PY - 2010/3/18/entrez PY - 2010/3/18/pubmed PY - 2010/8/6/medline SP - 1232 EP - 9 JF - Chemistry, an Asian journal JO - Chem Asian J VL - 5 IS - 5 N2 - (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-propyltrimethoxysilyl)-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. SN - 1861-471X UR - https://www.unboundmedicine.com/medline/citation/20235277/_R___+__Binol_functionalized_mesoporous_organosilica_as_a_highly_efficient_pre_chiral_catalyst_for_asymmetric_catalysis_ L2 - https://doi.org/10.1002/asia.200900737 DB - PRIME DP - Unbound Medicine ER -