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

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The focus of this project is to advance understanding of the mechanisms and selectivities of recently introduced reactions, on the investigation of new reactions, and on the use of new reactions to produce novel scaffolds, materials, ligands, and catalysts. The research will include studies on the regioselectivity of [5+2] cycloadditions, studies of new 5- and 3-carbon agents for new [5+2] and [3+2] cycloadditions, serial [5+2]/[4+2] cycloadditions and a new [5+2]/Nazarov process for one step syntheses of [5.3.0] systems, studies on [3+2] cycloadditions of vinylaziridines (VA), Lewis acid mediated [3+2] cycloadditions of VAs, metal catalyzed [2+2+2+2] cycloadditions to produce cyclooctatetraenes and the use of these to make new materials, ligands, and catalysts. With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Professor Paul Wender in the Department of Chemistry at Stanford University. Professor Wender's research seeks to create new ways of doing synthesis and to use that expertise to advance the frontiers of chemistry, biology, medicine and materials science. New reactions offer 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. At its most fundamental level, synthesis provides the opportunity to create new compounds with functions that advance knowledge of chemistry and open opportunities for the preparation of materials of value to our society including probes, medicines, materials, fine chemicals, agricultural chemicals, and functional devices.