Premium
Adsorption of a Chiral Amine on Alginate Gel Beads and Evaluation of its Efficiency as Heterogeneous Enantioselective Catalyst
Author(s) -
Aguilera Daniel Antonio,
Spinozzi Di Sante Lisa,
Pettignano Asja,
Riccioli Riccardo,
Roeske Joël,
Albergati Luce,
Corti Vasco,
Fochi Mariafrancesca,
Bernardi Luca,
Quignard Françoise,
Tanchoux Nathalie
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900247
Subject(s) - chemistry , catalysis , enantioselective synthesis , biopolymer , amine gas treating , adsorption , covalent bond , heterogeneous catalysis , tertiary amine , organocatalysis , organic chemistry , combinatorial chemistry , polymer chemistry , polymer
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.