Enantioselective Conjugate Addition of Aromatic Amines to N-Alkenoyloxazolidinones Catalyzed by Iodido(binaphtholato)samarium

• Published in: European Journal of Organic Chemistry Vol. 2008; no. 3; pp. 532 - 539
• Main Authors: Reboule, Iréna, Gil, Richard, Collin, Jacqueline
• Format: Book Review Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.01.2008; WILEY‐VCH Verlag; Wiley
• Subjects: Amines; Asymmetric catalysis; Chemistry; Chemistry, Organic; Conjugate addition; Lanthanides; Michael addition; Physical Sciences; Samarium; Science & Technology; Michael addition; TANDEM REACTIONS; AZA-MICHAEL REACTION; ASYMMETRIC-SYNTHESIS; ALPHA,BETA-UNSATURATED KETONES; amines; LANTHANIDE COMPLEXES; CARBONYL-COMPOUNDS; asymmetric catalysis; conjugate addition; lanthanides; O-BENZYLHYDROXYLAMINE; MESO-EPOXIDES; PART 1; samaritan; AMIDATE COMPLEXES
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.200700861

Iodido(binaphtholato)samarium catalyzes the Michael addition of aromatic amines to N‐alkenoyloxazolidinones affording β‐amino acid derivatives with enantiomeric excesses of up to 88 %. A study of the effect of temperature on the asymmetric induction revealed an isoinversion in two reactions. The observation of a non‐linear effect suggests an equilibrium between several active species including dimers.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)