【9th.July】New Chemistry beyond Metathesis Catalyzed by Ruthenium Alkylidenes
日期：2016-07-09
阅读：449
TOPIC：New Chemistry beyond Metathesis Catalyzed by Ruthenium Alkylidenes
SPEAKER：Prof. Daesung Lee, University of Illinois at Chicago, USA
TIME：July 9 (Saturday) AM10:30
LOCATION：Room 528, Chemistry Building A (化学A楼528演讲厅)
INVITER：A. Prof. Changkun Li (李长坤 特别研究员)
Biography
Education
1988 BS, Chemistry, Seoul National University, Seoul, Korea
1990 MS, Chemistry, Seoul National University, Seoul, Korea
1998 PhD, Chemistry, Stanford University Advisor: Prof. Paul A. Wender; Thesis: “Synthetic Studies on Taxol and Its Analogues”
1998–2000 Postdoctoral Fellow, Chemistry, Harvard University Advisor: Prof. Stuart L. Schreiber, Research in Diversity-Oriented Synthesis
Professional Experience
06/2000–05/2007 Assistant Professor of Chemistry, University of Wisconsin-Madison, WI 06/2007–07/2014 Associate Professor of Chemistry, University of Illinois at Chicago, IL
08/2014–now Professor of Chemistry, University of Illinois at Chicago, IL
Research Interest
Development of new synthetic methods and their application to natural product syntheses. Metathesis chemistry and metallotropic shift. Carbene-based transformations. Aryne-based benzannulation reactions
Honors and Awards
Alfred P. Sloan Foundation Research Fellowship (2005) Camille and Henry Dreyfus New Faculty Award (2000) Syntex Graduate Fellowship (1993)
Abstract
The main utility of Grubbs-type ruthenium alkylidenes involves metathesis chemistry. These ruthenium complexes, however, have proven their potential as a precatalyst for many non-metathetic transformations such as hydrogenation, dihydroxylation, and cyclopropanation. In light of expanding the scope of enyne metathesis, we streamlined enyne metathesis and metallotropic [1,3]-shift such that various enyne-based functional groups could be constructed by the tandem catalysis of ruthenium alkylidenes. While exploring these tandem reactions of bis-1,3-diyne substrates, unprecedented hydrovinylation reaction was discovered when ethylene was employed as an alkene counterpart. More interestingly, these bis-1,3-diynes could undergo hexadehydro Diels-Alder reaction to form aryne intermediates, which were hydrohalogenated by ruthenium alkylidenes complexes in the presence of halohydrocarbons. In this presentation, the scope and utility of these powerful and novel transformations will be discussed in the context of their discovery and application to natural product synthesis.
