title: On the role of DNA in DNA-based catalytic enantioselective conjugate addition reactions.
abstract: A kinetic study of DNA-based catalytic enantioselective Friedel-Crafts alkylation and Michael addition reactions showed that DNA affects the rate of these reactions significantly. Whereas in the presence of DNA, a large acceleration was found for the Friedel-Crafts alkylation and a modest acceleration in the Michael addition of dimethyl malonate, a deceleration was observed when using nitromethane as nucleophile. Also, the enantioselectivities proved to be dependent on the DNA sequence. In comparison with the previously reported Diels-Alder reaction, the results presented here suggest that DNA plays a similar role in both cycloaddition and conjugate addition reactions.
authors.affiliation: Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands.
authors.forename: Ewold W
authors.initials: EW
authors.lastname: Dijk
authors.forename: Arnold J
authors.initials: AJ
authors.lastname: Boersma
authors.forename: Ben L
authors.initials: BL
authors.lastname: Feringa
authors.forename: Gerard
authors.initials: G
authors.lastname: Roelfes
mesh_terms: D000478:Alkylation; D002384:Catalysis; D004247:DNA / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D004247:DNA