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© 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.

Abstract

The improvement of the catalytic activity of a heterogeneous chiral catalyst is one of the most critical issues, as are its recovery and reuse. The design of a heterogeneous chiral catalyst, including the immobilization method and the support polymer, is of significance for the catalytic activity in asymmetric reactions. An ionic, core-corona polymer microsphere-immobilized MacMillan catalyst (ICCC) was successfully synthesized by the neutralization reaction of sulfonic acid functionalized core-corona polymer microsphere (CCM–SO3H) with a chiral imidazolidinone precursor. We selected the core-corona polymer microsphere as the polymer support for the improvement of catalytic activity and recovery. The MacMillan catalyst was immobilized onto the pendant position of the corona with ionic bonding. ICCC exhibited excellent enantioselectivity up to 92% enantiomeric excess (ee) (exo) and >99% ee (endo) in the asymmetric Diels-Alder (DA) reaction of (E)-cinnamaldehyde and 1,3-cyclopentadiene. ICCC was quantitatively recovered by centrifugation because of the microsphere structure. The recovered ICCC was reused without significant loss of the enantioselectivity.

Details

Title
Ionic, Core-Corona Polymer Microsphere-Immobilized MacMillan Catalyst for Asymmetric Diels-Alder Reaction
Author
Md Wali Ullah
First page
960
Publication year
2019
Publication date
2019
Publisher
MDPI AG
e-ISSN
20734344
Source type
Scholarly Journal
Language of publication
English
ProQuest document ID
2547503069
Copyright
© 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.