Development of sustainable synthetic methods: Construction of 4-dihydropyridinones and β-amino esters by domino reactions in aqueous ethanol

ORGN 532

Peter J. Alaimo, alaimop@seattleu.edu, Robert V O'Brien III, obri1371@seattleu.edu, Adam Johnson, john2250@seattleu.edu, Sarah Slauson, slausons@seattleu.edu, Jamie O'Brien, garciaj@seattleu.edu, Elizabeth Tyson, tysone@seattleu.edu, Jon Chacon, Lorien Wallace, wallacel@seattleu.edu, and Sarah Connell. Department of Chemistry, Seattle University, 901 12th Avenue, Seattle, WA 98122
Over the past 15 years, sustainable synthetic methods have become an important frontier in organic chemistry. The aim of green chemistry is to eliminate the adverse effects of chemical synthesis on the environment. In this regard, impressive progress has been made through the use of reusable catalysts, renewable resources, and alternative solvents. Other significant advances include eliminating the generation of toxic byproducts through the discovery of safer reactions and reagents, developing more efficient reactions (e.g., catalyzed reactions), and using domino reaction cascades. Despite the widespread use of domino reactions, reaction byproducts have never been internally recycled in a domino reaction to catalyze a subsequent reaction in a domino cascade. We will present an efficient, green synthetic method that utilizes this idea of internal recycling to generate beta-amino esters and 4-dihydropyridinones.