期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 9, 期 20, 页码 4862-4867出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200304937
关键词
amino acid derivative; catalysis; chirality; Michael addition; stereoselectivity
Extensive investigations of chiral auxiliaries and active metals for Michael addition of 1,3-dicarbonyl compounds with vinyl ketones are summarized. Our efforts result in a widely applicable auxiliary-mediated, copper(II) acetate-catalyzed procedure. For these purposes, L-valine diethylamide is an optimal chiral auxiliary giving quaternary stereocenters with up to 99% ee at ambient temperature. No inert or anhydrous conditions are required, the solvent is simply acetone, and the auxiliary can be recovered almost quantitatively after workup.
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