Asymmetric Transition Metal-Catalyzed Allylic Alkylations

Born in Philadelphia, PA, in 1941 where he began his university training at the University of Pennsylvania (BA, 1962), Barry M. Trost obtained a Ph.D. degree in Chemistry just three years later at the Massachusetts Institute of Technology (1965). He directly moved to the University of Wisconsin where he was promoted to Professor of Chemistry in 1969 and subsequently became the Vilas Research Professor in 1982. He joined the faculty at Stanford as Professor of Chemistry in 1987 and became Tamaki Professor of Humanities and Sciences in 1990. In addition, he has been Visiting Professor of Chemistry in Germany (Universities of Marburg, Hamburg, and Munich), Denmark (University of Copenhagen), France (Universities of Paris VI and Paris-Sud), Italy (University of Pisa), and Spain (University of Barcelona). In 1994 he was presented with a Docteur honoris causa of the Université Claude-Bernard (Lyon I), France. Professor Trost made a major contribution early in his career with the isolation, structure determination, and synthesis of the insect juvenile hormone which initiated the concept of insect growth regulants as an alternative to pesticides. Enhancing synthetic effectiveness has been a major goal. How can the ever increasing complex molecules needed to meet the needs of society in an economical and practical fashion be created? Developing the tools, i.e., the reactions and reagents, that enhance selectivity and impart “atom economy” is the first stage. He has pursued this goal in many ways with a major thrust being the rational design of selective catalysts which may make them the “chemists' enzymes”. Inserting sulfur substituents to impart synthetic versatility has created the concept of organosulfones as chemical chameleonsi.e., serving as both nucleophiles and electrophiles depending upon the environment. Coordinating a set of reactions into a sequence that permits the construction of a complex target from readily available starting materials represents the second and final stage. Over 100 total syntheses of divergent molecules ranging from antitumor agents to electrical conductors have been completed.

David L. Van Vranken was born in St. Charles, MO, in 1965. He received his B.S. degree from the University of Texas at Austin in 1987 and his Ph.D. at Stanford under the direction of Barry M. Trost as an NSF graduate fellow. His graduate work centered around the development of enantioselective palladium catalysis and the synthesis of aminocyclopentitol glycosidase inhibitors. He then did his postdoctoral with Peter G. Schultz at Berkeley as an NSF postdoctoral fellow before accepting his current position at UC Irvine. His current research interests center around the development of peptide Mannich reactions in proteins and in natural products synthesis.