A short olefin metathesis-based route to enantiomerically pure arylated dihydropyrans and alpha, beta-unsaturated delta-valero lactones.
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.
Wildemann
Holger
H
FB Chemie der Universität Dortmund, Organische Chemie, D-44221 Dortmund, Germany.
Dünkelmann
Pascal
P
Müller
Michael
M
Schmidt
Bernd
B