An Environmentally Friendly Procedure for the Synthesis of Nitrogen-­Containing Molecules

Due to the prevalence of nitrogen containing molecules within the carbon framework in pharmaceuticals, our group has developed novel approaches to the construction of such molecules using readily available starting materials and benign reagents while minimizing the production of waste by-products.  We discovered that under mild reaction conditions (5 mol % CuCl, 1.25 mol % pyridine, THF, air, and room temperature), the starting hydroxamic acid oxidizes to form an acylnitroso compound in situ.  We hypothesize that these mild reaction conditions will allow for the expansion of acylnitroso chemistry to include numerous reaction platforms.  This presentation will report our efforts in this area and the development of an asymmetric acylnitroso aldol reaction using Evans’ chiral auxiliary.