Iridium-Catalyzed Asymmetric Hydrogenation of Olefins

Stephen Roseblade was born in Kettering, UK, in 1977. He is a graduate of the University of Oxford, where he worked with Jeremy Robertson, and received a PhD from the University of Bristol having completed his thesis under the direction of Varinder Aggarwal. After a stay at the University of Seville, as a Marie Curie Fellow, he joined the research group of Andreas Pfaltz at the University of Basel as a post-doctoral research associate. His research interests include synthetic organic chemistry and asymmetric catalysis.

Andreas Pfaltz was born in Basel, Switzerland, in 1948. He received a diploma in natural sciences and a PhD degree from the ETH in Zürich. After completing his thesis under the direction of Albert Eschenmoser in 1978, he joined the research group of Gilbert Stork at Columbia University as a postdoctoral fellow. In 1980 he returned to the ETH where he was appointed “Privatdozent” (Lecturer) in 1987. From 1990 to 1995 he was Professor of Organic Chemistry at the University of Basel and from 1995 to 1998 director at the Max-Planck-Institut für Kohlenforschung in Mülheim an der Ruhr, Germany. In 1999 he returned to the University of Basel where he is currently Professor of Chemistry.

Asymmetric hydrogenation is one of the most important catalytic methods for the preparation of optically active compounds. For a long time the range of olefins that could be hydrogenated with high enantiomeric excess was limited to substrates bearing a coordinating group next to the CC bond. We have found a new class of catalysts, iridium complexes with chiral P, N ligands, that overcome these limitations. For a wide range of unfunctionalized olefins, excellent enantioselectivities could be achieved. Because these catalysts do not require the presence of any particular functional group in the substrate, they considerably broaden the scope of asymmetric hydrogenation. In addition, promising results were also obtained with certain functionalized alkenes, furans, and benzofurans.