Adsorption of a Chiral Amine on Alginate Gel Beads and Evaluation of its Efficiency as Heterogeneous Enantioselective Catalyst - Université de Montpellier Accéder directement au contenu
Article Dans Une Revue European Journal of Organic Chemistry Année : 2019

Adsorption of a Chiral Amine on Alginate Gel Beads and Evaluation of its Efficiency as Heterogeneous Enantioselective Catalyst

Résumé

An organic catalyst derived from quinine can be adsorbed on alginate gels by following a simple protocol. The resulting solvogel beads are competent and highly stereoselective catalysts for an asymmetric Michael reaction. 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 organocatalytic processes.

Domaines

Chimie
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Dates et versions

hal-02280121 , version 1 (06-09-2019)

Identifiants

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Daniel Antonio Aguilera, Lisa Spinozzi Di Sante, Asja Pettignano, Riccardo Riccioli, Joël Roeske, et al.. Adsorption of a Chiral Amine on Alginate Gel Beads and Evaluation of its Efficiency as Heterogeneous Enantioselective Catalyst. European Journal of Organic Chemistry, 2019, 2019 (24), pp.3842-3849. ⟨10.1002/ejoc.201900247⟩. ⟨hal-02280121⟩
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