Heterogeneous asymmetric Henry reaction using a chiral bis(oxazoline)-copper complex immobilized on magnetically separable mesocellular mesoporous silica support

Jun Mun Lee; Jaeyun Kim; Yongje Shin; Chang Eun Yeom; Ji Eun Lee; Taeghwan Hyeon; B. Moon Kim

doi:10.1016/j.tetasy.2010.01.024

Heterogeneous asymmetric Henry reaction using a chiral bis(oxazoline)-copper complex immobilized on magnetically separable mesocellular mesoporous silica support

Jun Mun Lee, Jaeyun Kim, Yongje Shin, Chang Eun Yeom, Ji Eun Lee, Taeghwan Hyeon, B. Moon Kim

Seoul National University

Research output: Contribution to journal › Article › peer-review

51 Scopus citations

Abstract

A chiral bis(oxazoline) ligand was immobilized onto a magnetically separable hierarchically-ordered mesocellular mesoporous silica (M-HMMS) and this new catalytic system was examined in the asymmetric Henry reaction between various aldehydes and nitromethane at ambient temperature. Good enantioselectivity (upto 86.0% ee) was observed when the free silanol groups of the mesoporous silica were capped by trimethylsilyl group. This catalyst was separated magnetically and reused several times without significant loss of reactivity or enantioselectivity. This magnetic separation of catalysts could lead to further development toward practical industrial scale application due to simplicity without cumbersome filtration.

Original language	English
Pages (from-to)	285-291
Number of pages	7
Journal	Tetrahedron Asymmetry
Volume	21
Issue number	3
DOIs	https://doi.org/10.1016/j.tetasy.2010.01.024
State	Published - 1 Mar 2010
Externally published	Yes

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10.1016/j.tetasy.2010.01.024

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title = "Heterogeneous asymmetric Henry reaction using a chiral bis(oxazoline)-copper complex immobilized on magnetically separable mesocellular mesoporous silica support",

abstract = "A chiral bis(oxazoline) ligand was immobilized onto a magnetically separable hierarchically-ordered mesocellular mesoporous silica (M-HMMS) and this new catalytic system was examined in the asymmetric Henry reaction between various aldehydes and nitromethane at ambient temperature. Good enantioselectivity (upto 86.0\% ee) was observed when the free silanol groups of the mesoporous silica were capped by trimethylsilyl group. This catalyst was separated magnetically and reused several times without significant loss of reactivity or enantioselectivity. This magnetic separation of catalysts could lead to further development toward practical industrial scale application due to simplicity without cumbersome filtration.",

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T1 - Heterogeneous asymmetric Henry reaction using a chiral bis(oxazoline)-copper complex immobilized on magnetically separable mesocellular mesoporous silica support

AU - Lee, Jun Mun

AU - Kim, Jaeyun

AU - Shin, Yongje

AU - Yeom, Chang Eun

AU - Lee, Ji Eun

AU - Hyeon, Taeghwan

AU - Moon Kim, B.

PY - 2010/3/1

Y1 - 2010/3/1

N2 - A chiral bis(oxazoline) ligand was immobilized onto a magnetically separable hierarchically-ordered mesocellular mesoporous silica (M-HMMS) and this new catalytic system was examined in the asymmetric Henry reaction between various aldehydes and nitromethane at ambient temperature. Good enantioselectivity (upto 86.0% ee) was observed when the free silanol groups of the mesoporous silica were capped by trimethylsilyl group. This catalyst was separated magnetically and reused several times without significant loss of reactivity or enantioselectivity. This magnetic separation of catalysts could lead to further development toward practical industrial scale application due to simplicity without cumbersome filtration.

AB - A chiral bis(oxazoline) ligand was immobilized onto a magnetically separable hierarchically-ordered mesocellular mesoporous silica (M-HMMS) and this new catalytic system was examined in the asymmetric Henry reaction between various aldehydes and nitromethane at ambient temperature. Good enantioselectivity (upto 86.0% ee) was observed when the free silanol groups of the mesoporous silica were capped by trimethylsilyl group. This catalyst was separated magnetically and reused several times without significant loss of reactivity or enantioselectivity. This magnetic separation of catalysts could lead to further development toward practical industrial scale application due to simplicity without cumbersome filtration.

UR - https://www.scopus.com/pages/publications/77949307801

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DO - 10.1016/j.tetasy.2010.01.024

M3 - Article

AN - SCOPUS:77949307801

SN - 0957-4166

VL - 21

SP - 285

EP - 291

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 3

ER -

Heterogeneous asymmetric Henry reaction using a chiral bis(oxazoline)-copper complex immobilized on magnetically separable mesocellular mesoporous silica support

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