Abstract
A range of substituted cycloalkene-1,1-dicarboxylat es was synthesized through olefin metathesis starting from readily available acylic malonate pre cursors in an efficient fashion. As a metathesis catalyst, a Grubbs II-type catalyst was used in the se experiments, which were run in water and gave the cyclic malonate products with high convers ions of 94-100%. The catalytic amount was in the range of 0.5-5 mol% dependent on the structu re 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-sub stituted prochiral cycloalkene-1,1dicarboxylates.
Highlights
Metathesis reactions in water have gained increasing interest in the last years,[1,2,3,4,5,6,7,8,9,10,11,12,13,14,15] and provide a range of advantages such as a high potential for the development of sustainable syntheses
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%
We reported the proof of concept for such an one-pot process combining metathesis and enzymatic hydrolysis reactions exemplified for the synthesis of cycloalkene-1,1-dicarboxylate monoesters starting from readily available bis-substituted malonates (Scheme 1).[14]
Summary
Metathesis reactions in water have gained increasing interest in the last years,[1,2,3,4,5,6,7,8,9,10,11,12,13,14,15] and provide a range of advantages such as a high potential for the development of sustainable syntheses. In this paper we report our results addressing these issues, demonstrating the generality of this metathesis reaction in water as a suitable solvent by the preparation of a variety of such sterically more complex prochiral cyclic malonates of type 2, bearing a substituent at the cycloalkene ring.
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