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A short olefin metathesis-based route to enantiomerically pure arylated dihydropyrans and alpha, beta-unsaturated delta-valero lactones. 2003

Holger Wildemann, and Pascal Dünkelmann, and Michael Müller, and Bernd Schmidt
FB Chemie der Universität Dortmund, Organische Chemie, D-44221 Dortmund, Germany.

The synthesis of arylated dihydropyrans and unsaturated lactones starting from enantiomerically pure alpha-hydroxy ketones (prepared by an enzyme-catalyzed benzoin condensation) is described. The key steps are a highly diastereoselective addition of vinyl metal compounds under chelate control and a ruthenium-catalyzed ring-closing olefin metathesis reaction. Elucidation of the relative configuration of the final products was achieved by NOE experiments.

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