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.