Synthesis of new chiral monodentate phosphines and their use in asymmetric hydrogenation

✍ Scribed by Kathrin Junge; Günther Oehme; Axel Monsees; Thomas Riermeier; Uwe Dingerdissen; Matthias Beller

• Book ID: 104251361
• Publisher: Elsevier Science
• Year: 2002
• Tongue: French
• Weight: 74 KB
• Volume: 43
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(02)00943-7

✦ Synopsis

A general synthesis of chiral 4,5-dihydro-3H-dinaphthophosphepines 1a-g is described. The resulting ligands represent a new class of monodentate chiral phosphines. First applications of 1a-g in the rhodium-catalyzed asymmetric hydrogenation of unsaturated carboxylic acid derivatives demonstrate the usefulness of our ligands. Enantioselectivities up to 95% ee for the hydrogenation of methyl a-acetamidocinnamate were obtained in the presence of 1d. This result represents one of the highest enantioselectivities reported for asymmetric hydrogenation in the presence of monodentate phosphines.