Synthesis of substituted cycloalkene-1,1-dicarboxylates via olefin metathesis in water

Abstract

A range of substituted cycloalkene-1,1-dicarboxylates was synthesized through olefin metathesis starting from readily available acylic malonate precursors in an efficient fashion. As a metathesis catalyst, a Grubbs II-type catalyst was used in these experiments, which were run in water and gave the cyclic malonate products with high conversions of 94-100%. The catalytic amount was in the range of 0.5-5 mol% dependent on the structure of the starting material. The generality of this metathesis reaction in water was demonstrated as well as its suitability for the preparation of five and six-membered and alkyl as well as aryl-substituted prochiral cycloalkene-1,1-dicarboxylates.