Cycloruthenated compounds as efficient catalyst for asymmetric hydride transfer reaction*
Jean-Baptiste Sortais1, Laurent Barloy1, Claude Sirlin1, André H. M. de Vries2, Johannes G. de Vries2, and Michel Pfeffer1
1CNRS, UMR 7177, Laboratoire de Synthèses Métallo-Induites, Université Louis Pasteur, 4, rue Blaise Pascal, 67000 Strasbourg, France; 2DSM Pharmaceutical Chemicals, Advanced Synthesis, Catalysis, and Development, P.O. Box 18, 6160 MD Geleen, The Netherlands
Abstract: Cycloruthenated complexes obtained by direct C-H activation of enantiopure aromatic primary and secondary amines are efficient catalysts in asymmetric hydride transfer reaction. Reduction of acetophenone has been achieved rapidly with enantiomeric excesses (ee's) ranging from 38 to 89 %. The importance of Ru-C bond in the catalytic efficiency is highlighted.
Keywords: cyclometallation; chirality; enantioselectivity; ketones; high-throughput experiments; reduction; catalysis; amines; ruthenium.
*Pure Appl. Chem. 78, 197-523. An issue of reviews and research papers based on lectures presented at the 13th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-13), Geneva, Switzerland, 17-21 July 2005.