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Article Dans Une Revue Chemical Communications Année : 2015

DNA-cellulose: an economical, fully recyclable and highly effective chiral biomaterial for asymmetric catalysis

Résumé

The challenge in DNA-based asymmetric catalysis is to perform a reaction in the vicinity of the helix by incorporating a small-molecule catalyst anchored to the DNA in a covalent, dative, or non-covalent yet stable fashion in order to ensure high levels of enantio-discrimination. Here, we report the first generation of a DNA-based catalyst bound to a cellulose matrix. The chiral biomaterial is commercially available, trivial to use, fully recyclable and produces high levels of enantioselectivity in various Cu(II)-catalyzed asymmetric reactions including Friedel–Crafts alkylations and Michael additions. A single-pass, continuous-flow process is also reported affording fast conversions and high enantioselectivities at low catalyst loadings thus offering a new benchmark in the field of DNA-based asymmetric catalysis.

Domaines

Chimie
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Dates et versions

hal-03554623 , version 1 (31-01-2024)

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Erica Benedetti, Nicolas Duchemin, Lucas Bethge, Stefan Vonhoff, Sven Klussmann, et al.. DNA-cellulose: an economical, fully recyclable and highly effective chiral biomaterial for asymmetric catalysis. Chemical Communications, 2015, 51 (28), pp.6076-6079. ⟨10.1039/C4CC10190A⟩. ⟨hal-03554623⟩
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