Publication: Chiral Pyrrolidine Bridged Polyhedral Oligomeric Silsesquioxanes as Heterogeneous Catalysts for Asymmetric Michael Additions
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Issued Date
2018-02-01
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1572879X
1011372X
1011372X
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2-s2.0-85039713811
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Mahidol University
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SCOPUS
Bibliographic Citation
Catalysis Letters. Vol.148, No.2 (2018), 779-786
Suggested Citation
Torsak Luanphaisarnnont, Sasikarn Hanprasit, Vetiga Somjit, Vuthichai Ervithayasuporn Chiral Pyrrolidine Bridged Polyhedral Oligomeric Silsesquioxanes as Heterogeneous Catalysts for Asymmetric Michael Additions. Catalysis Letters. Vol.148, No.2 (2018), 779-786. doi:10.1007/s10562-017-2286-z Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/45437
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Chiral Pyrrolidine Bridged Polyhedral Oligomeric Silsesquioxanes as Heterogeneous Catalysts for Asymmetric Michael Additions
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Abstract
© 2017, Springer Science+Business Media, LLC, part of Springer Nature. Abstract: A chiral pyrrolidine bridged polyhedral oligomeric silsesquioxane (SQ) was synthesized, characterized, and used as an effective heterogeneous catalyst. The synthesis involves two simple steps: nucleophilic substitution between benzylchloride functionalized SQ and imidazoyl pyrrolidine carboxylate and subsequent deprotection. The catalyst was isolated by simple filtration. The SQ-supported chiral pyrrolidine catalyst was used as a heterogeneous catalyst in an asymmetric Michael addition into nitrostyrenes under room temperature and neat condition, giving the product in excellent yields (85–91%), diastereoselectivities (up to 99:1) and enantioselectivities (95–98%). The catalyst can be recycled by a simple filtration without a significant loss in its reactivity and selectivity.