Approaches to Improved Synthesis Design: Mechanistic and Synthetic Studies on New Annelation Methods

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The focus of this research is to advance understanding of the mechanisms and selectivities of recently introduced reactions, on the investigation of newly identified reactions, and on the identification of new reactions including intermolecular allenyl- and alkenyl-vinylcyclopropane (VCP) [5+2] cycloadditions; allenyl-VCP-CO [5+2+1] cycloadditions; asymmetric [5+2] cycloadditions; metathetical processes for the generation of VCPs and VCBs (vinylcyclobutanes); [4+2+1] cycloadditions of dienes, alkenes, and CO; allene-diene-CO [2+2+1] cycloadditions; 3-component reactions based on dienes and allenes; [6+1] reactions of allenylcyclobutanes; carbonylative allenyl ether transpositions; [5+1+2+1] cycloadditions; [3+2]/[5+1] reactions; and the use of 4-component cycloadducts as ligands for catalysis and molecular recognition.With this renewal award, the Organic and Macromolecular Chemistry Program is supporting the research and educational activities of Dr. Paul A. Wender in the Department of Chemistry at Stanford University. Professor Wender will focus his work on the design or discovery and development of fundamentally new reactions, reagents, and strategies for organic synthesis. The continuing emphasis of the project is on the identification of new reactions as new reactions enable new synthetic strategies and better if not ideal syntheses (high yielding, step economical, resource effective, operationally simple and environmentally acceptable) of targets of theoretical, materials, or medicinal value. A special emphasis is placed on catalyzed reactions, especially processes that in the absence of catalyst are forbidden or difficult to achieve. The introduction of new reactions offers new ways to think about synthetic problems, new process options that could minimize or avoid environmentally problematic steps and process inefficiencies, and often new mechanisms and insights that add to our basic knowledge of bonding, structure, and reactivity. The project has broader impact by engaging in education from outreach to high school students through the training of postdoctoral participants. Scientific impact on the chemical, pharmaceutical and agricultural industries will also accrue