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Synfacts 2015; 11(7): 0773
DOI: 10.1055/s-0034-1380997
DOI: 10.1055/s-0034-1380997
Polymer-Supported Synthesis
A Cellulose-Supported DNA-Based Ligand for Asymmetric Catalysis
Benedetti E, Duchemin N, Bethge L, Vonhoff S, Klussmann S, Vasseur J.-J, Cossy J, Smietana M, * Arseniyadis S. * NOXXON Pharma AG, Berlin, Germany Universités Montpellier and PSL Research University, Paris, France
DNA-Cellulose: An Economical, Fully Recyclable and Highly Effective Chiral Biomaterial for Asymmetric Catalysis.
Chem. Commun. 2015;
51: 6076-6079
DNA-Cellulose: An Economical, Fully Recyclable and Highly Effective Chiral Biomaterial for Asymmetric Catalysis.
Chem. Commun. 2015;
51: 6076-6079
Further Information
Publication History
Publication Date:
17 June 2015 (online)
Significance
Copper-catalyzed asymmetric Friedel–Crafts alkylations (eq. 1) and Michael additions (eq. 2) proceeded in the presence of cellulose-supported calf thymus DNA and 4,4′-dimethyl-2,2′-bipyridine (dmbpy) to give the corresponding alkylation products with up to >99% conversion and up to 97% ee.
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Comment
In the formation of compound A, the catalyst was recovered and reused nine times without adding any copper or dmbpy. Compound A was also prepared in 96% conversion and up to 80% ee by a continuous-flow process using the DNA-based catalyst packed in a medium-pressure liquid chromatography cartridge (residence time: 38 min, room temperature).
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