Synthesis of new chiral monodentate aminophosphinites and their use in catalytic asymmetric hydrogenations

A general synthesis of chiral 4-amino-4,5-dihydro-3H-dinaphthophosphepines 5a-f is described. The resulting monodentate chiral aminophosphinites have been tested in the rhodium-catalyzed asymmetric hydrogenation of methyl alpha-acetamidocinnamate and methyl alpha-acetamidoacrylate. Enantioselectivities up to 96% ee were obtained in the presence of 5a and sodium dodecylsulfonate in toluene. (C) 2003 Elsevier Science B.V. All rights reserved.