The first catalytic enantioselective addition of ?-dicarbonyl compounds to alkynones is presented. The conjugate addition proceeds in very high yields, giving a mixture of (Z)- and (E)-enones with up to 95% ee using the cinchona alkaloid [DHQ]2PHAL (5 mol %) as the catalyst. This organocatalytic enantioselective reaction has been further developed to a one-pot procedure to give the optically active (E)-enone adduct using first [DHQ]2PHAL (5 mol %), followed by Bu3P (10 mol %), as the catalysts.
Organocatalytic enantioselective conjugate addition to alkynones / Bella, Marco; Jorgensen, Ka. - In: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY. - ISSN 0002-7863. - 126:(2004), pp. 5672-5673. [10.1021/ja0493594]
Organocatalytic enantioselective conjugate addition to alkynones
BELLA, Marco;
2004
Abstract
The first catalytic enantioselective addition of ?-dicarbonyl compounds to alkynones is presented. The conjugate addition proceeds in very high yields, giving a mixture of (Z)- and (E)-enones with up to 95% ee using the cinchona alkaloid [DHQ]2PHAL (5 mol %) as the catalyst. This organocatalytic enantioselective reaction has been further developed to a one-pot procedure to give the optically active (E)-enone adduct using first [DHQ]2PHAL (5 mol %), followed by Bu3P (10 mol %), as the catalysts.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
