title: DNA-cellulose: an economical, fully recyclable and highly effective chiral biomaterial for asymmetric catalysis.
abstract: 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.
authors.affiliation: Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI) - ESPCI ParisTech/CNRS (UMR8231)/PSL* Research University, 10 rue Vauquelin, 75231 Paris Cedex 05, France. stellios.arseniyadis@espci.fr.
authors.forename: Erica
authors.initials: E
authors.lastname: Benedetti
authors.forename: Nicolas
authors.initials: N
authors.lastname: Duchemin
authors.forename: Lucas
authors.initials: L
authors.lastname: Bethge
authors.forename: Stefan
authors.initials: S
authors.lastname: Vonhoff
authors.forename: Sven
authors.initials: S
authors.lastname: Klussmann
authors.forename: Jean-Jacques
authors.initials: JJ
authors.lastname: Vasseur
authors.forename: Janine
authors.initials: J
authors.lastname: Cossy
authors.forename: Michael
authors.initials: M
authors.lastname: Smietana
authors.forename: Stellios
authors.initials: S
authors.lastname: Arseniyadis
mesh_terms: D000478:Alkylation; D000818:Animals; D002384:Catalysis; D002417:Cattle; D002482:Cellulose / Q000737:chemistry*; D003300:Copper / Q000737:chemistry*; D004247:DNA / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D009942:Organometallic Compounds; D003300:Copper; D002482:Cellulose; D004247:DNA; C427203:calf thymus DNA