Diastereoselective C-arylation of prochiral enolates by the SRN1 reaction

✍ Scribed by María T. Baumgartner; Guillermo A. Lotz; Sara M. Palacios

• Publisher: John Wiley and Sons
• Year: 2004
• Tongue: English
• Weight: 327 KB
• Volume: 16
• Category: Article
• ISSN: 0899-0042
• DOI: 10.1002/chir.20011

✦ Synopsis

Abstract

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 (4__R__,5__S__)‐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. Chirality 16:212–219, 2004. © 2004 Wiley‐Liss, Inc.