On the role of DNA in DNA-based catalytic enantioselective conjugate addition reactions.
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.
Dijk
Ewold W
EW
Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands.
Boersma
Arnold J
AJ
Feringa
Ben L
BL
Roelfes
Gerard
G
D000478:Alkylation; D002384:Catalysis; D004247:DNA / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D004247:DNA