Diastereoselective C-arylation of prochiral enolates by the SRN1 reaction.

BAUMGARTNER, M.T.*; LOTZ, G.A.; PALACIOS, S.M.*

WILEY-LISS

Lugar: NEW YORK; Año: 2004 vol. 16 p. 212 - 212

hiral phenyl acetamide enolate ions were diastereoselectively arylated using aromatic substrates by means of the SRN1 reaction. The substitution took place with a diastereomeric excess that varied from 31 to 98% depending on the enolate counterion, the reaction temperature, the solvent and the aromatic substrate. The absolute configuration of the new stereogenic center of the products (4R,5S)-1,5-dimethyl-4-phenyl-3-[2’-phenyl-2’-arylacetyl]-imidazolidin-2-one (Aryl= 3-quinolyl, 1-naphthyl, 4-anisyl, 4-benzonitryl, 4-tolyl, 9-phenanthryl) was determined by 1H NMR spectroscopy and theoretical calculations.