Adsorption of a chiral amine on alginate gel beads and evaluation of its efficiency as heterogeneous enantioselective catalyst

Aguilera, Daniel Antonio (Department of Industrial Chemistry “Toso Montanari” & INSTM RU Bologna, Alma Mater Studiorum, University of Bologna, Bologna, Italy ; Institut Charles Gerhardt, CNRS-ENSCM-UM, Montpellier, France) ; Spinozzi Di Sante, Lisa (Department of Industrial Chemistry “Toso Montanari” & INSTM RU Bologna, Alma Mater Studiorum, University of Bologna, Bologna, Italy) ; Pettignano, Asja (Department of Industrial Chemistry “Toso Montanari” & INSTM RU Bologna, Alma Mater Studiorum, University of Bologna, Bologna, Italy ; Institut Charles Gerhardt, CNRS-ENSCM-UM, Montpellier, France) ; Riccioli, Riccardo (Department of Industrial Chemistry “Toso Montanari” & INSTM RU Bologna, Alma Mater Studiorum, University of Bologna, Bologna, Italy) ; Roeske, Joël (Department of Industrial Chemistry “Toso Montanari” & INSTM RU Bologna, Alma Mater Studiorum, University of Bologna, Bologna, Italy ; School of Engineering and Architecture (HEIA-FR), HES-SO // University of Applied Sciences Western Switzerland) ; Albergati, Luce (Department of Industrial Chemistry “Toso Montanari” & INSTM RU Bologna, Alma Mater Studiorum, University of Bologna, Bologna, Italy ; School of Engineering and Architecture (HEIA-FR), HES-SO // University of Applied Sciences Western Switzerland) ; Corti, Vasco (Department of Industrial Chemistry “Toso Montanari” & INSTM RU Bologna, Alma Mater Studiorum, University of Bologna, Bologna, Italy) ; Fochi, Mariafrancesca (Department of Industrial Chemistry “Toso Montanari” & INSTM RU Bologna, Alma Mater Studiorum, University of Bologna, Bologna, Italy) ; Bernardi, Luca (Department of Industrial Chemistry “Toso Montanari” & INSTM RU Bologna, Alma Mater Studiorum, University of Bologna, Bologna, Italy) ; Quignard, Françoise (Institut Charles Gerhardt, CNRS-ENSCM-UM, Montpellier, France) ; Tanchoux, Nathalie (Institut Charles Gerhardt, CNRS-ENSCM-UM, Montpellier, France)

A representative Lewis base organic catalyst (9-amino-9-deoxy epi-quinine, QNA) can be adsorbed in high yields onto acidic alginate gels (AGs) using a very simple and straightforward protocol. The resulting solvogel beads (QNA@AGs) are active as heterogeneous catalysts in the addition of aldehydes to nitroalkenes, affording the corresponding adducts in good yields and moderate to excellent diastereo- and enantio-selectivities. In these reactions, the carboxylic functions of the biopolymer act as both acidic co-catalyst and non-covalent anchoring site for the tertiary amine catalyst (as observed by IR spectroscopy). Use of heterocationic gels, derived from alkaline earth metal gels by proton exchange, provided materials with better mechanical properties and higher porosities, ultimately resulting in higher catalytic activities. This work represents the first utilization of alginates, abundant and renewable biopolymers, as gel supports/media for asymmetric or-ganocatalytic processes.


Article Type:
scientifique
Faculty:
Ingénierie et Architecture
School:
HEIA-FR
Institute:
ChemTech - Institut des technologies chimiques
Subject(s):
Ingénierie
Date:
2019-04
Pagination:
8 p.
Published in:
European Journal of Organic Chemistry
Numeration (vol. no.):
2019, issue 24, pp. 3842-3849
DOI:
ISSN:
1434-193X
Appears in Collection:

Note: The status of this file is: restricted


 Record created 2019-07-02, last modified 2019-07-02

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