5.27 Ene–Yne Metathesis

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Abstract

Ene–yne metathesis (EYM) is an efficient catalytic method for diene synthesis using simple unsaturated reactants. The reaction shows excellent functional group tolerance characteristic of the Grubbs ruthenium carbenes. That the ruthenium carbenes are widely available and easy to use explains the widespread application of EYM in organic chemistry. Successful ring-closing applications have led to increased use of EYM in total synthesis. Some of the synthetic appeal is due to the accessibility of the simple reactants and the use of the resulting 1,3-dienes in subsequent transformation including cascade reactions. Combined metathesis sequences or tandem reactions provide a rapid gain in structural complexity using a catalytic reaction as the key carbon–carbon bond-forming step. The successful application of EYM in complex molecule synthesis combined with continuing improvements in substrate scope and a refined understanding of reaction mechanism has made EYM a useful synthetic method for C–C bond construction. This chapter reviews the literature of EYM and provides an overview of the reactions' capabilities.

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Steven T. Diver grew up in Salt Lake City, Utah, and attended the University of Utah where he received his bachelor's degree in chemistry. From there, he went on to doctoral studies with Prof. Edwin Vedejs at the University of Wisconsin–Madison. Diver then took up a postdoctoral position with Prof. Stuart Schreiber at Harvard, where he became interested in metathesis reactions. He started his independent career at the University at Buffalo (SUNY-Buffalo) in 1997, where he is currently Full Professor. His group is interested in diene synthesis by EYM, synthetic applications, and understanding how the reaction works. Outside the laboratory, Diver enjoys spending time with his family and keeps active with distance running and cycling.

Joseph R. Clark was born in Rochester, NY, in 1986. He received his BS in chemistry from St. John Fisher College in 2008. Near the end of his undergraduate studies, he worked in Prof. Diver's laboratory for 10 weeks during the summer of 2007 as an National Science Foundation-Research Experiences for Undergraduates (NSF-REU) undergraduate researcher. This is where he was first introduced to EYM and the experience helped stimulate him to pursue doctoral studies in organic chemistry. Joe Clark is currently a third-year graduate student at the University at Buffalo–The State University of New York investigating EYM and new diene functionalization reactions under the direction of Prof. Steven T. Diver.

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