Asymmetric Oxidative C-C Bond Forming Reactions

Nature uses oxidative couplings to construct carbon-carbon, carbon-oxygen, and carbon-nitrogen bonds with a high degree of efficiency. Surprisingly, few laboratory equivalents are as selective or as efficient as the biological versions. Our lab studies oxidative fragment couplings that give rise to complexity rapidly. 

New reactions are discovered through specific hypotheses and through broader hypotheses that are especially enable by High Throughput Experimentation.  The unexpected outcomes obtained highlight the value of interrogating large numbers of rationally selected variables under the umbrella of general hypothesis. 

The development of selective catalytic processes has been achieved for asymmetric naphthol coupling, phenol coupling, asymmetric phenol coupling, oxindole coupling, N-arylation, and alkyl C–H activation that utilize environmentally sustainable oxygen as the terminal oxidant. Applications in total synthesis include phleichrome, cercosporin, hypocrellin A, shiraiachrome A, nigerone, bisoranjidiol, bismahanine core, honokiol, chaetoglobin, carpanones, pulchelstyrene D, spirolouveline, 10-hydroxy-11-methoxydracaenone, salutaridine analogs, and pyrolaside B. Finally, studies on the mechanisms of these transformations will be described with the goal of understanding the governing principles and how they might be used to discover further new transformations.