Diastereoselective C-arylation of prochiral enolates by the SRN1 reaction.
Chiral phenyl acetamide enolate ions were diastereoselectively arylated using aromatic substrates by means of the S(RN)1 reaction. The substitution took place with a diastereomeric excess that varied from 31-98%, 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 (1)H NMR spectroscopy and theoretical calculations.
Baumgartner
María T
MT
INFIQC, Depto. de Química Orgánica, U.N.C. Ciudad Universitaria, Universidad Nacional de Córdoba, Argentina. tere@dqo.fcq.unc.edu.ar
Lotz
Guillermo A
GA
Palacios
Sara M
SM