Progress toward tandem nitro reduction, imine formation, nucleophilic addition in the synthesis of beta-amino esters

ORGN 547

Jamie M. Garcia, garciaj@seattleu.edu and Peter J. Alaimo, alaimop@seattleu.edu. Department of Chemistry, Seattle University, 901 12th Avenue, Seattle, WA 98122
The environmentally benign synthesis of β-amino carbonyl compounds via tandem nitro-reduction/Mannich reactions is being investigated. β-Amino carbonyl compounds are biologically and synthetically important compounds, having wide applications in the synthesis of numerous pharmaceuticals and natural products. A unique feature of this reaction is the recycling of indium (III) byproducts of the nitro reduction step as catalysts for imine formation and subsequent condensation. Each step of this reaction has been explored individually; however, combining nitro reduction with imine formation and reaction with the silylketene acetal in a one-pot synthesis has not been reported. We will report our progress investigating this domino synthesis, along with reaction optimization efforts.
 

Heterocycles, Aromatics, Metal-Mediated Reactions and Syntheses, Materials, Devices, and Switches
8:00 PM-10:00 PM, Wednesday, 29 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 27 March 2006 Georgia World Congress Center -- Ex. Hall B4, Sci-Mix

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006