A short olefin metathesis-based route to enantiomerically pure arylated dihydropyrans and a,ß-unsaturated delta-Valero lactones

Wildemann, H.; Schmidt, B.; Dünkelmann, P.; Müller, M.

doi:10.1021/jo0264729

Journal Article

A short olefin metathesis-based route to enantiomerically pure arylated dihydropyrans and a,ß-unsaturated delta-Valero lactones

Wildemann, H. ; Dünkelmann, P.FZJ* ; Müller, M.FZJ* ; Schmidt, B.

2003
American Chemical Society [S.l.]

The journal of organic chemistry 68, 799 - 804 (2003) [10.1021/jo0264729]

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Please use a persistent id in citations: http://hdl.handle.net/2128/2434 doi:10.1021/jo0264729

Abstract: 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.

Keyword(s): J

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