Our group uses allenes as tools for exploring important issues in contemporary organic synthesis. For example, our efforts to develop new allene amination methods led to the discovery of silver complexes capable of catalyst-controlled and tunable chemoselective C-N bond-forming reactions. The ability of silver to adopt a multitude of different coordination geometries allowed us to extend this chemoselectivity to favor reaction at one site of unsaturation over another, to choose between amination of a C-H or a C=C bond or even tune for reactivity between two C-H bonds. Allenes have also proven to be powerful platforms for accessing an array of aminated building blocks for the construction of bioactive molecules. Our efforts in developing highly regio-, chemo- and stereocontrolled allene aziridination methods for the preparation of libraries of densely functionalized aminocyclitols and other complex amines related to pactamycin and jogyamycin will be described.

Oxidative allene amination in the synthesis of complex molecules

248th National Meeting (2014)

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