Enantiomerically Enriched Allylic Alcohols and Allylic Amines via C–C Bond-Forming Hydrogenation: Asymmetric Carbonyl and Imine Vinylation

Eduardas Skucas obtained a B.S. degree in chemistry from Temple University, Philadelphia, PA, where he conducted undergraduate research under the tutelage of Professor Franklin Davis. In Fall 2005, he initiated graduate studies at the University of Texas at Austin under the supervision of Professor Michael J. Krische, where he is involved in the discovery and development of new C–C bond-forming hydrogenations.

Ming-Yu Ngai obtained a B.S. degree in chemistry at the University of Hong Kong (HKU), where he conducted undergraduate research under the tutelage of Professor Chi-Ming Che. During his undergraduate study, Ming-Yu Ngai spent 1 year abroad at the University of California, San Diego, under the supervision of Professor Michael VanNieuwenhze. In Fall 2004, he initiated graduate studies at the University of Texas at Austin under the supervision of Professor Michael J. Krische, where he is involved in the discovery and development of new C–C bond-forming hydrogenations.

Venukrishnan Komanduri obtained a B.S. degree in chemistry from Andhra Loyola College, Vijayawada, India, and an M.S. degree from the Indian Institute of Technology (IIT), Chennai, India. In Fall 2002, he initiated graduate studies at Wayne State University, under the tutelage of Professor Maarten H. D. Postema. In Fall 2004, he continued graduate studies at the University of Texas at Austin under the supervision of Professor Michael J. Krische, where he is involved in the discovery of new C–C bond-forming hydrogenations.

Michael Krische obtained a B.S. degree in chemistry from the University of California at Berkeley, where he performed research under the tutelage of Professor Henry Rapoport. After 1 year of study abroad as a Fulbright Fellow, he initiated graduate study at Stanford University under the mentorship of Professor Barry Trost as a Veatch Graduate Fellow. Following his Ph.D. degree, he engaged in postdoctoral studies with Jean-Marie Lehn at the Université Louis Pasteur as an NIH Postdoctoral Fellow. In Fall 1999, Professor Krische was appointed as Assistant Professor of Chemistry at the University of Texas at Austin. He was promoted directly to Full Professor in Fall 2004. His research on hydrogenative C–C coupling has received recognition in the form of numerous awards: Elias J. Corey Award (2007), Dowpharma Prize (2007), Presidential Green Chemistry Award (2007), Solvias Ligand Prize (2006), Society of Synthetic Chemistry Japan Lectureship (2005), Johnson & Johnson Focused Giving Award (2005), Dreyfus Teacher Scholar Award (2003), Alfred P. Sloan Research Fellowship (2003), Cottrell Scholar Award (2002), Frasch Foundation Award in Chemistry (2002), Lilly Grantee Award (2002), and National Science Foundation–CAREER Award (2000).

Hydrogenation of alkynes in the presence of carbonyl compounds and imines using cationic rhodium(I) and iridium(I) precatalysts enables the formation of allylic alcohols and allylic amines, respectively. Through the use of hydrogenation catalysts modified by chiral ligands, allylic alcohols and allylic amines may be generated in highly optically enriched forms. Hydrogenative fragment couplings of this type circumvent the use of preformed organometallic reagents and avoid the generation of stoichiometric byproducts.